Organoboron chemistry: 1 Boron-oxygen and boron-sulfur compounds
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| 1. Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
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New York [u.a.]
Interscience Publ.
1964
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| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXXII, 950 S. Ill. |
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| 041 | 0 | |a eng | |
| 049 | |a DE-29T |a DE-20 |a DE-188 |a DE-11 | ||
| 100 | 1 | |a Steinberg, Howard |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Organoboron chemistry |n 1 |p Boron-oxygen and boron-sulfur compounds |c Howard Steinberg |
| 264 | 1 | |a New York [u.a.] |b Interscience Publ. |c 1964 | |
| 300 | |a XXXII, 950 S. |b Ill. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 773 | 0 | 8 | |w (DE-604)BV009379761 |g 1 |
| 856 | 4 | 2 | |m HBZ Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006224786&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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| adam_text | Titel: Bd. 1. Organoboron chemistry. Boron-oxygen and boron-sulfur compounds
Autor: Steinberg, Howard
Jahr: 1964
CONTENTS
1.
Introduction
.........
1
I.
General
Remarks
.......
1
II.
Scope
of
Series
.......
3
III.
Literature
Coverage
.......
5
IV.
References
........
5
2.
Configuration
and
General
Nature
of
Compounds
...
7
I.
General
Nature
.......
7
II.
Configuration
........
7
III.
Comparison
of
Organic
and
Organoboron
Structures
.
10
IV.
References
.
.
.
.
.
.
.
.11
3.
Nomenclature
.........
12
I.
Introduction
.
.
.
.
.
.
.
.12
II.
Trigonal
Coplanar
Compounds—Boron
Atom
not
in
a
Ring
.........
14
A.
Compounds
Containing
One
Boron
Atom
.
.
14
B.
Compounds
Containing
More
Than
One
Boron
Atom
16
III.
Boron
Radicals
.......
16
IV.
Trigonal
Coplanar
Compounds—Boron
Atom
in
a
Ring
17
A.
Four-
to
Ten-Membered
Rings
.
...
17
B.
Larger
Rings
.......
20
C.
Bicyclic
Compounds
......
20
D.
Spiro
Compounds
......
20
E.
Sugar
Derivatives
.
.
.
.
.
21
F.
Trivial
Names
.......
21
V.
Tetrahedral
Compounds
......
22
A.
Addition
Compounds
(Lewis
Acid-Base
Complexes)
22
B.
Coordination
Compounds
.....
22
1.
Unidentate
ligands
.....
22
2.
Bidentate
ligands
......
24
3.
Terdentate
ligands
.....
25
C.
Boronium
Salts
.......
25
VI.
References
.
.
.
.
.
•
•
.26
4.
Symmetrical
Orthoborates
of
Monohydric
Alcohols
and
Phenols
27
I.
Introduction
........
27
II.
Historical
........
28
1*
ix
x
Contents
III.
Properties
........
28
A.
General
........
28
B.
Structure
........
32
IV.
Methods
of
Preparation
......
34
A.
From
Boric
Acid
......
34
1.
Methods
of
water
removal
....
34
2.
Rate
of
esterification
.....
36
3.
Mechanism
.......
37
4.
Trimethoxyborane
.....
38
5.
Separation
of
the
trimethoxyborane-methanol
Azeotrope
.......
41
6.
Triethoxyborane
......
44
7.
Tripropoxyborane
and
tri-r-butoxyborane
.
45
8.
Reaction
with
esters
of
inorganic
acids
.
.
45
9.
Reaction
with
enols
.....
46
10.
Condensation
with
formaldehyde
and
carbon
monoxide
.
.
.
.
.
47
B.
From
Metaboric
Acid
......
47
C.
From
Boric
Oxide
......
48
1.
No
water
removal
.....
48
2.
Water
removal
......
50
3.
Effect
of
azeotroping
agent
....
51
4.
Reaction
with
esters
of
inorganic
acids
.
.
52
D.
From
Borax
and
Related
Compounds
...
52
E.
Transesterification
......
54
1.
Examples
.
.
.
.
.
.
.55
2.
Mechanism
.......
59
3.
Alkoxy
sources
other
than
alcohols
.
.
63
F.
From
Triacetoxyborane
.....
65
G.
From
Boron
Trihalides
.....
66
1.
Boron
trichloride
and
alcohols
or
phenols
.
67
a.
Solvents
.......
69
b.
Mechanism
......
69
c.
Effect
of
amines
.....
72
d.
Boron
trichloride
complexes
and
alcohols
.
74
2.
Boron
tribromide
and
trifluoride
and
alcohols
.
75
3.
Reaction
with
alkoxides
....
75
4.
Reaction
with
ethers
.
.
.
.
.76
a.
Boron
trichloride
.....
76
b.
Boron
tribromide
.....
78
c.
Boron
trifluoride
.
.
.
.
.78
d.
Mechanism
......
78
5.
Reaction
with
cyclic
ethers
....
82
6.
Reaction
with
alkoxysilanes
....
86
7.
Reaction
with
aldehydes
....
87
Contents
xi
8.
Reaction
with
esters
.....
88
9.
Reaction
with
sodium
trimethoxyhydroborate
.
89
10.
Reaction
with
silver
isocyanate
...
89
H.
From
Alkoxyhaloboranes
.
.
.
.
.90
1.
Disproportionation
.....
90
a.
Alkoxychloroboranes
....
90
b.
Aryloxyhaloboranes
.....
92
c.
Alkoxyfluoroboranes
....
94
2.
Decomposition
.
.
.
.
.
.
95
a.
Factors
influencing
stability
...
95
b.
Mechanism
......
98
c.
2-Chloro-l,3,2-dioxaborolanes
and
borinanes
100
d.
Aryloxyhaloboranes
.....
101
3.
Alcoholysis
.......
101
4.
Reduction
.......
101
5.
Reaction
with
carboxybc
acids
.
.
.
101
I.
From
Trialkoxyboroxines
.....
102
1.
Disproportionation
.
.
.
.
.
102
2.
Alcoholysis
.......
103
3.
Partial
hydrolysis
.....
104
4.
Reaction
with
sodium
hydride
.
.
.
104
5.
Reaction
with
sodium
borohydride
.
.
104
6.
Reaction
with
sodium
trimethoxyhydroborate
.
104
J.
From
Hydridic
Compounds
.
.
.
.
.
105
1.
Alkoxyboranes
......
105
a.
Disproportionation
.....
105
b.
Alcoholysis
......
106
2.
Alcoholysis
of
boron
hydrides
.
.
.
107
a.
Diborane
and
borane
complexes
.
.107
b.
Higher
boron
hydrides
....
108
c.
Metal
borohydrides
.....
109
3.
Reaction
of
diborane
and
tetrahydrofurans
.
109
4.
Reaction
of
diborane
and
sodium
trimethoxy¬
hydroborate
or
sodium
tetramethoxyborate
.
110
5.
Reactions
of
boron
hydrides
and
ketones
.
110
6.
Sodium
trialkoxyhydroborates
.
.
.
110
7.
Hydroxylamine-borane
complexes
.
.
.111
K.
From
Tetraalkoxyborates
.
.
.
.
.111
L.
From
Boron-Carbon
Compounds
.
.
.
.112
1.
Disproportionation
.
.
.
.
.112
2.
Reaction
with
diborane
....
113
3.
Alcoholysis
.
.
.
.
.
.
.113
4.
Oxidation
.......
114
5.
Thermal
decomposition.
.
.
.
.115
6.
Reaction
with
hydrogen
chloride
.
.
.115
Contents
xii
M.
From
Boron-Nitrogen
Compounds
.
.
.115
N.
From
Boron-Sulfur
Compounds
.
.
.
.116
O.
From
B-O-P
Compounds
.
.
.
.
.116
P.
From
Diboron
Compounds
.
.
.
.116
Q.
From
Tri(alkylperoxy)boranes
.
.
.
.117
R.
From
Unsymmetrioal
Orthoborates
.
.
.117
S.
As
a
Means
of
Separating
and
Purifying
Alcohols
.
118
V.
Reactions
........
118
A.
Thermal
Stability
.
.
.
.
.
.118
1.
Elimination
.......
118
2.
Ether
formation
......
122
3.
Reverse
aldol
reaction
.....
123
B.
Hydrolysis
.......
123
C.
Alcoholysis
.
.
.
.
.
.
.123
D.
With
Amines
.......
124
1.
Complex
formation
....
.
124
a.
Trimethoxyborane
.
.
.
.
.124
b.
Higher
trialkoxyboranes
....
125
c.
Triaryloxyboranes
.
.
.
.
.127
2.
Displacement
.
.
.
.
.
.129
a.
Amino
alcohols
.
.
.
.
.132
b.
Amino
acids
.
.....
134
c.
Mechanism
.
.
.
.
.
.
134
3.
Other
reactions
......
136
E.
With
Acids.....
.
.137
1.
Carboxylic
acids
.
.
.
.
.
.137
2.
Sulfuric
acid
......
138
3.
Phosphoric
acid
.
.
.
.
.
.
139
4.
Nitric
acid
.......
139
5.
Hydrogen
chloride
.....
139
6.
Hydrogen
bromide
and
iodide
.
.
.
140
7.
Hydrogen
fluoride
.
.
.
.
.140
8.
Boric
acid
.......
141
F.
With
Acid
Anhydrides
.....
141
G.
With
Esters
.......
141
1.
Borates
.......
141
2.
Silicates
.......
142
3.
Carboxylates
.
.
.
.
.
.142
H.
With
Aldehydes
and
Ketones
....
142
I.
With
Acetals
.......
143
J.
With
Ethers
.......
143
K.
With
Hydroperoxides
......
143
L.
With
Alkoxides
......
143
M.
With
Hydroxides
.
.
.
.
.
.143
N.
With
Halogen
Compounds
.....
144
Contents
xiii
1.
The
halogens
......
144
2.
Group
I
halides
......
144
3.
Group
II
halides
......
144
4.
Group
III
halides
......
145
5.
Group
IV
halides
.....
145
6.
Group
V
halides
......
145
7.
Thionyl
chloride
......
146
8.
Alkyl
halides
......
146
9.
Acyl
halides.......
146
10.
Alkoxydihaloboranes
.....
147
O.
With
Silicon
Compounds
.....
147
P.
With
Nitriles
.......
147
Q.
With
Metals
.......
147
1.
Sodium
.......
147
2.
Mercury
.......
148
R.
With
Organometallic
Reagents
....
148
S.
With
Hydric
Compounds
.....
148
1.
Metal
hydrides
......
148
2.
Boron
hydrides
......
149
T.
With
Diazoalkanes
......
149
U.
With
Sulfur
Compounds
.....
151
V.
With
Boron-Carbon
Compounds
....
151
W.
With
Boron-Nitrogen
Compounds
.
.
.
152
X.
Friedel-Crafts
Reaction
.
.
.
.152
Y.
Oxidation
........
155
Z.
Reduction........
155
AA.
Of
Unsaturated
Esters
.....
155
1.
Addition
.......
155
2.
Polymerization
......
156
3.
Copolymerization
.....
157
BB.
Of
Tri(mercaptoalkoxy)boranes
....
157
VI.
Analytical
........
158
A.
Hydrolytically
Unstable
“Neutral”
Esters
.
.
158
B.
Hydrolytically
Unstable
“Acidic”
or
“Basic”
Esters
158
C.
Hydrolytically
Stable
Esters
....
159
VII.
Physical
Constants
.......
161
A.
Trialoxyboranes.
.
.
.
.
•
.161
B.
Triaryloxyboranes
......
181
C.
Amine
Complexes
of
Trialkoxyboranes
.
.
.191
D.
Amine
Complexes
of
Triaryloxyboranes
.
.192
VIII.
References
........
200
5.
Orthoborates
of
Polyhydric
Alcohols
and
Phenols
.217
I.
Orthoborates
Derived
from
Dihydric
Alcohols
and
Phenols
217
A.
Introduction
.......
217
B.
Historical
217
XIV
Contents
C.
Properties
....••••
218
D.
Methods
of
Preparation
.....
221
1.
Introduction
......
221
2.
Prom
boric
acid
......
221
3.
Prom
boric
oxide
.....
223
4.
From
boric
acid
esters
.
.
.
?
•
223
5.
Prom
triacetoxyborane
.....
224
6.
From
boron
trichloride
and
its
derivatives
.
225
7.
Prom
1,3,2-dioxaborolane
and
borinane
deriva¬
tives
........
226
8.
Prom
sodium
borohydride
reduction
of
diketones
226
E.
Reactions
........
227
1.
Thermal
stability
......
227
2.
Hydrolysis
.......
227
3.
Alcoholysis
.......
227
4.
With
amines
......
227
5.
With
trialkoxyboranes
.
.
.
•
•
228
6.
With
hydrogen
bromide
....
228
7.
With
trialkylboranes
.....
228
8.
Friedel-Craffcs
alkylation
....
228
9.
Miscellaneous
......
228
H.
Orthoborates
Derived
from
Trihydric
Alcohols
.
229
A.
Introduction
.......
229
B.
Historical
........
229
C.
Glyceryl
Borate
.......
230
D.
Trimethylolethane
Borate
.....
232
E.
Triethanolamine
Borate
.....
232
1.
Properties
.......
232
a.
General
.......
232
b.
Structure
......
233
2.
Methods
of
preparation
.....
235
3.
Reactions
.......
236
P.
Triethanolamine
Borate
Derivatives
.
.
.
237
G.
Triisopropanolamine
Borate
....
242
1.
Properties
.......
242
a.
General
.......
242
b.
Structure
......
242
2.
Methods
of
preparation
.....
242
H.
Tri-n-propanolamine
Borate
....
244
I.
Polymers
........
244
III.
Orthoborates
Derived
from
Tetrahydric
Alcohols
.
245
IV.
Sugar
Borates
........
245
V.
Analytical
........
246
VI.
Physical
Constants
.......
247
A.
Orthoborates
Derived
from
Dihydric
Alcohols
and
Phenols
.......
247
Contents
xv
B.
Orthoborates
Derived
from
Trihydric
Alcohols
and
Phenols
........
253
VII.
References
........
259
6.
Unsymmetrical
Orthoborates
......
262
I.
Introduction
........
262
II.
Esters
Derived
from
Monohydric
Alcohols
and
Mono-
hydric
Phenols
.......
262
A.
Historical
........
262
B.
Methods
of
Preparation
.....
263
C.
Reactions
........
266
D.
Hindered
Phenolic
Borates
.....
267
III.
Esters
Derived
from
Dihydric
Alcohols
and
Dihydric
Phenols
.........
270
A.
Unsymmetrical
Biborates
.....
270
B.
Hydroxy
Derivatives
......
272
IV.
Esters
Derived
from
Mono-
and
Dihydric
Alcohols
and
Phenols
.........
275
A.
2-Alkoxy-l,3,2-dioxaborolanes
and
Borinanes
.
.
275
1.
Introduction
.
.
.
.
.
.275
2.
Properties
.......
276
3.
Methods
of
preparation
.....
278
a.
From
boric
acid
or
equivalent
.
.
.278
b.
From
2-hydroxy-l,3,2-dioxaborolanes
and
borinanes
.
.
.
.
.
.279
c.
By
transesterification
of
trialkoxyboranes
.
281
d.
By
transesterification
of
2-alkoxy-l,3,2-di-
oxaborolanes
......
282
e.
From
trialkoxyboranes
and
glycol
biborates.
283
f.
Thermal
decomposition
of
tris-((3-chloro-
methoxyethoxy)borane
....
284
g.
From
alkoxydihaloboranes
.
.
.
284
h.
From
2-halo-1,3,2-dioxaborolanes
and
borinanes
......
284
i.
From
2,2 -oxybis-(l,3,2-dioxaborlanes)
.
285
j.
From
alkoxyhydroxyboranes
.
.
.
286
k.
From
2-alkylthio-l,3,2-dioxaborolanes
.
286
l.
From
diketones
and
diborane
.
.
•
286
4.
Reactions
.......
286
a.
Thermal
stability
.....
286
b.
Hydrolysis
......
288
c.
Alcoholysis
and
thioalcoholysis
.
.
.
289
d.
With
amines
......
289
e.
With
boron
trihalides
....
291
f.
With
alkoxychloroboranes
....
291
g.
With
alkali
metals
.....
291
XVI
Contents
h.
With
Grignard
reagent
i.
Friedel-Crafts
alkylation
.
j.
With
tropolones
....
k.
Miscellaneous
.....
B.
Alkylenedioxybis(dialkoxyboranes)
1.
Introduction
.....
2.
Methods
of
preparation
....
V.
Esters
Derived
from
Mono-
and
Trihydric
Alcohols
VI.
Analytical
.......
VII.
Physical
Constants
......
VIII.
References
.......
291
291
293
293
293
293
293
294
294
295
327
7.
Alkoxyhydroxyboranes,
2-Hydroxy-l,3,2-dioxaborolanes
and
Borinanes
and
Their
Anhydrides
and
Salts
I.
Introduction
......
II.
Dialkoxyhydroxyboranes
and
Their
Anhydrides
III.
Alkoxydihydroxyboranes
....
A.
From
Monohydric
Alcohols
and
Phenols
B.
From
Polyhydric
Alcohols
and
Phenols
IV.
2-Hydroxy-1,3,2-dioxaborolanes
and
Borinanes
and
Re¬
lated
Compounds
.....
A.
Historical
......
B.
Properties
......
C.
Methods
of
Preparation
1.
From
diols
and
boric
acid
or
equivalent
2.
From
polyols
and
boric
acid
.
3.
By
partial
hydrolysis
a.
Orthoborates
....
b.
Oxybis(dioxaborolanes
and
borinanes)
c.
2-Chloro-l,3,2-dioxaborolanes
4.
From
Alkylenedioxydihydroxyborates
D.
Reactions
......
1.
Hydrolysis
.....
2.
Dehydration.
....
3.
Salt
formation
....
4.
Esterification
....
5.
Acetylation
.....
V.
Salts
of
2-Hydroxy-l,3,2-dioxaborolanes
and
Borinanes
and
Related
Compounds
....
A.
Properties
......
1.
Structure
.....
2.
Solubility
.....
B.
Methods
of
Preparation
1.
From
diols
and
triols
and
borate
salts
2.
From
polyols
....
3.
From
2-hydroxy-l,3,2-dioxaborolanes
and
bori¬
nanes
........
330
330
330
331
331
332
334
334
335
337
337
340
341
341
343
343
343
344
344
344
344
344
345
346
346
346
347
349
349
351
352
Contents
xvii
a.
And
metallic
sodium.....
352
b.
And
metal
hydroxides
....
352
c.
And
metal
methoxides
....
352
d.
And
alkali
metal
tetraborates
353
e.
And
ammonia
......
353
C.
Reactions
........
353
1.
Hydrolysis
......
353
2.
With
strong
acid
......
354
3.
With
methyl
iodide
.....
354
VI.
2,2 -Oxybis-(l,3,2-dioxaborolanes
and
borinanes)
.
354
A.
Properties
........
354
B.
Methods
of
Preparation
.....
355
1.
Prom
diols
and
boric
acid
or
equivalent
.
2.
Prom
2-hydroxy-l,3,2-dioxaborolanes
and
bori¬
355
nanes
........
355
a.
Dehydration
......
355
b.
And
2-chloro-l,3,2-dioxaborolanes
355
3.
Prom
oxybis(diacetoxyborane)
356
4.
From
trialkoxyboranes
.....
356
C.
Reactions
........
356
1.
Hydrolysis
.......
356
2.
Alcoholysis
.......
357
3.
Pyrolysis
.......
358
4.
With
amines
......
359
5.
With
boron
halides
.....
359
6.
Miscellaneous
......
359
VII.
Analytical
........
360
A.
Boron
Determination
......
360
B.
Karl
Fischer
Determination
.....
360
VIII.
Physical
Constants
.......
362
IX.
References
........
386
Acyloxy
Derivatives
........
389
I.
Introduction
........
389
II.
Triacyloxyboranes
and
Oxybis(diacyloxyboranes)
390
A.
Historical
........
390
B.
Properties
........
391
1.
General
.......
391
2.
Structure
.......
391
C.
Methods
of
Preparation
.....
394
1.
From
carboxylic
acid
anhydrides
394
2.
From
carboxylic
acid
chlorides
395
3.
From
carboxylic
acids
....
396
a.
And
chloroboranes
.....
396
b.
And
boron
tribromide
....
397
c.
And
diborane
......
397
xviii
Contents
d.
And
trialkylboranes
.....
397
e.
And
triacetoxyborane
....
398
4.
From
carboxylic
acid
esters
....
398
5.
From
carboxylic
acid
salts
....
399
6.
From
ketene
......
399
D.
Reactions
........
399
1.
Hydrolysis
.......
399
2.
Alcoholysis
.......
400
3.
Thermal
stability
......
400
4.
With
amines
......
402
5.
With
carboxylic
acids
and
carboxylic
acid
chlorides
.......
402
6.
Friedel-Crafts
......
402
7.
With
sodium
methoxide
....
403
8.
Reduction
.......
403
a.
Hydrogenation.
.....
403
b.
With
diborane
or
sodium
borohydride
.
403
9.
With
esters
of
inorganic
acids
.
.
.
403
10.
As
a
catalyst
......
404
11.
Complex
formation
.
.
.
.
.
405
12.
Miscellaneous
......
405
E.
Analytical........
405
1.
Boron
........
405
2.
Karl
Fischer......406
III.
Acyloxyhydroxyboranes
.
.
.
.
.
406
IV.
Diacyloxyaryloxyboranes
.
.
.
.
.
•
407
A.
Properties
........
407
B.
Methods
of
Preparation
.....
407
C.
Reactions
........
416
1.
Hydrolysis
.......
416
2.
Thermal
stability
......
417
3.
With
carboxylic
acids
.....
418
V.
2-Acyloxy-l,3,2-dioxaborolanes
.....
418
A.
Properties
........
418
B.
Methods
of
Preparation
.....
419
C.
Reactions
........
419
VI.
Acyloxyboranes
Derived
from
Hydroxy
Acids
.
.
419
VII.
Acyloxyboranes
Derived
from
Dibasic
Acids
.
.
420
VIH.
Physical
Constants
.......
422
IX.
References
........
440
9.
Trialkoxyboroxines
and
Related
Compounds
....
443
I.
Trialkoxyboroxines
.......
443
A.
Introduction
.......
443
B.
Historical
........
443
C.
Properties
........
444
Contents
xix
1.
General
.......
444
2.
Structure
.......
444
D.
Methods
of
Preparation
.....
1.
From
monohydric
alcohols
or
phenols
and
boric
445
acid
or
equivalent
.....
445
2.
From
diols
or
triols
and
boric
acid
or
equivalent
447
3.
From
trialkoxyboranes
....
447
4.
From
trialkoxyboroxines
....
450
5.
From
alkoxyhaloboranes
....
451
a.
By
decomposition
.....
451
b.
Reaction
with
sodium
....
451
c.
Reaction
with
bis(trialkyltin)
oxides
.
452
6.
From
dioxane-boron
tribromide
complex.
452
7.
From
diacetoxyaryloxyboranes
452
8.
From
trialkylboroxines
.....
453
9.
From
diborane
and
carboxylic
acids
454
E.
Reactions
.......
454
1.
Hydrolysis
.......
454
2.
Alcoholysis
.......
454
3.
Disproportionation
.....
455
4.
Elimination
.......
455
5.
With
amines
......
458
6.
With
carboxylic
acids
and
derivatives
459
7.
With
halogen
compounds
....
459
a.
Chlorine
.......
459
b.
Hydrogen
halides
.....
459
c.
Boron
trihalides
.....
460
d.
Other
halides
......
460
8.
With
organometallic
reagents
460
9.
With
trialkylboranes
.....
460
10.
With
alkyldiboranes
.....
460
11.
Oxidation
.......
460
12.
Reduction
.......
461
13.
Miscellaneous
......
461
F.
Analytical
........
461
II.
Polyborates
........
462
A.
Introduction
.......
462
B.
Historical
........
462
C.
Properties
........
462
D.
Methods
of
Preparation
.....
463
1.
From
alcohols
and
boric
acid
or
equivalent
463
2.
From
trialkoxyboranes
.....
464
3.
From
trialkoxyboroxines
....
465
E.
Reactions
........
465
1.
Hydrolysis
.......
465
XX
Contents
2.
Thermal
decomposition
.....
465
III.
Triacyloxyboroxines.......
465
IV.
Physical
Constants
.......
467
V.
References
.
.
.
.
.
•
.476
10.
Peroxy
Derivatives
........
478
I.
Introduction
.
.
.
.
.
.
.
.478
II.
Properties
........
478
III.
Methods
of
Preparation
.
.
.
.
.
.478
A.
From
Alkyl
Hydroperoxides
and
Various
Boron
Sources
........
478
B.
By
Rearrangement
of
Alkyl(alkylperoxy)boranes
.
480
C.
Other
Attempts
.
.
.
.
.
.
.481
1.
From
dialkyl
peroxides
.
.
.
.
.481
2.
From
peracids
and
boron
trichloride
.
•
481
IV.
Reactions
........
481
A.
Hydrolysis
.......
481
B.
Alcoholysis
.......
481
C.
With
amines
.......
482
D.
Catalysis
of
polymerization
.....
482
V.
Analytical
........
482
VI.
Physical
Constants
.......
482
VII.
References
........
483
11.
Alkoxyboranes
.........
484
I.
Introduction
........
484
II.
Historical
........
484
III.
Properties
........
485
IV.
Methods
of
Preparation
......
485
A.
From
Diborane
.......
485
1.
And
alcohols
......
485
2.
And
other
oxygen
compounds
.
.
.
487
3.
And
trialkoxyboranes
.....
489
B.
From
Higher
Boron
Hydrides
....
490
C.
From
Dialkoxyhaloboranes
.....
492
D.
From
Sodium
Borohydride
and
Tertiary
Alcohols
.
492
E.
From
Sodium
Trimethoxyhydroborate
.
.
•
492
F.
From
Trialkoxyboranes
and
Reducing
Agents
.
493
G.
From
Trialkoxyboroxines
and
Reducing
Agents
.
493
V.
Reactions
........
493
A.
Hydrolysis
.......
493
B.
Alcoholysis
.......
494
C.
Disproportionation
......
494
D.
With
Amines
.......
494
E.
With
Hydrides,
Tetraalkoxyborates,
and
Tetra-
(alkoxyhydro)borates
......
494
Contents
xxi
F.
With
Olefins
and
Acetylenes
.
495
G.
With
Carbonyl
Compounds
and
Nitriles
.
495
H.
Hydrogen
Exchange
.
.
495
VI.
Analytical
.....
.
496
VII.
Physical
Constants
....
.
497
VIII.
References
.....
.
500
12.
Alkoxyhaloboranes
and
Related
Compounds
.
502
I.
Introduction
... ..
.
502
II.
Historical
.....
.
503
III.
Properties
.....
.
503
A.
General
.....
.
503
B.
Structure
.....
.
506
1.
Alkoxyehloroboranes
and
halosiloxyboranes
.
506
2.
Alkoxyfiuoroboranes
.
506
3.
2-Chloro-l,3,2-dioxaborolanes
and
borinanes
.
508
4.
Oxybis(acetoxychloroborane)
.
.
509
C.
Molecular
Refractivities
.
509
D.
Nuclear
Magnetic
Resonance
Data
511
E.
Bond
Energies
....
.
511
IV.
Alkoxy-
and
Aryloxydihaloboranes
.
512
A.
Methods
of
Preparation
.
512
1.
Introduction
.
512
2.
From
boron
trihalides
.
.
512
a.
And
alcohols,
glycols
and
phenols
.
512
b.
And
sodium
phenoxides
.
515
c.
And
ethers
.
515
d.
And
cyclic
ethers
.
520
e.
And
aldehydes
.
.
523
f.
And
ketones
.
524
g.
And
ß-ketoamides
.
525
h.
And
carboxylic
acid
esters
.
525
i.
And
alkoxysilanes
.
526
j.
And
alkyl
phosphites
527
k.
And
boronic
acid
esters
527
1.
And
trialkoxyboroxines
527
3.
From
trialkoxyboranes
.
527
a.
And
boron
trihalides.
527
b.
And
diphenyl
phosphonate
530
e.
And
various
chlorides
530
4.
From
dialkoxyhaloboranes
530
a.
And
boron
trihalides
530
d.
Disproportionation
.
530
B.
Reactions
.....
531
1.
Hydrolysis
....
531
2.
Alcoholysis
....
533
XXII
Contents
3.
With
alkoxides
......
533
4.
With
¿-butyl
hydroperoxide
....
533
5.
With
ethers
.......
533
6.
With
cyclic
ethers......
534
7.
With
bis(triethyltin)
oxide
....
534
8.
Thermal
decomposition
and
disproportionation
534
a.
Introduction
......
534
b.
Decomposition
to
alkyl
halides
.
.
.
535
c.
Other
decompositions
....
544
9.
With
amines
......
544
a.
Ammonia
......
544
b.
Primary
and
secondary
amines
.
.
.
544
c.
Tertiary
amines
.....
545
d.
Phenylhydrazine
.....
545
10.
With
carboxylic
acids
.....
546
11.
With
hydrogen
chloride
....
546
12.
With
thionyl
chloride
.
.
.
546
13.
Reduction
.......
546
a.
With
sodium
borohydride
....
546
b.
With
sodium
trimethoxyhydroborate
.
.
546
c.
With
sodium
......
546
14.
With
trialkoxyboranes
.
.
.
.
.
546
15.
With
dialkoxyalkylboranes
....
547
V.
Dialkoxy-
and
Diaryloxyhaloboranes
....
547
A.
Methods
of
Preparation
.....
547
1.
Prom
boron
trihalides
.....
547
a.
And
alcohols
or
phenols
....
547
b.
And
ethers
......
548
c.
And
cyclic
ethers
.
.
.
.
.
549
d.
And
alkoxysilanes
.....
549
e.
And
trialkoxy-
and
triaryloxyboranes
.
550
2.
Prom
alkoxy-
and
aryloxydihaloboranes
.
.551
a.
And
alcohols
and
phenols
....
551
b.
And
alkoxides
......
552
c.
And
cyclic
ethers
.....
552
d.
Disproportionation
.....
552
e.
And
trialkoxyboranes
....
553
f.
And
boronic
acid
esters
....
553
3.
From
tri(polyfluoroalkoxy)boranes
.
.
.
553
B.
Reactions
........
553
1.
Hydrolysis
.......
553
2.
Alcoholysis
.......
554
3.
With
alkoxides
......
554
4.
With
¿-butyl
hydroperoxide
....
554
5.
With
ethers
.......
554
Contents
xxiii
6.
Disproportionation
.....
555
7.
Thermal
decomposition
.....
555
8.
With
amines
......
556
a.
Primary
and
secondary
....
556
b.
Tertiary
.......
556
9.
With
carboxylic
acids
.....
557
10.
With
hydrogen
chloride
....
557
11.
With
boron
trihalides
.....
557
12.
Reduction
.......
557
a.
With
sodium
......
557
b.
With
sodium
hydride
....
557
c.
With
sodium
borohydride
.
.
.
557
13.
With
sodium
tetramethoxyborate
.
.
.
558
VI.
Trialkylsiloxyhaloboranes
......
558
A.
Methods
of
Preparation
.....
558
1.
Boron
trihalide
cleavage
of
disiloxanes,
tri-
siloxanes
and
tetrasiloxanes
....
558
2.
Attempted
preparation
from
boron
trihalides
and
silanols
.......
559
B.
Reactions
........
560
1.
Hydrolysis
.......
560
2.
Alcoholysis
.......
560
3.
Disproportionation
.....
560
4.
Thermal
decomposition
.....
560
VII.
2-Halo-1,3,2-dioxaborolanes
and
borinanes
.
.
.
561
A.
Methods
of
Preparation
.....
561
1.
Prom
boron
trihalides
and
diols
or
catechol
.
561
2.
Prom
boron
trichloride
or
alkoxychloroboranes
and
2-alkoxy-l,3,2-dioxaborolanes
.
.
.
562
3.
From
2,2 -oxybis-(l,3,2-benzodioxaborole)
.
562
4.
Prom
ethylenedioxybisboranes
.
.
.
563
B.
Reactions
........
563
1.
Hydrolysis
.......
563
2.
Alcoholysis
.......
564
3.
With
thiols
.......
565
4.
Thermal
decomposition
.....
565
5.
With
amines
......
566
6.
With
carboxylic
acids
.....
566
7.
With
organometallic
reagents
.
.
.
567
8.
With
2-hydroxy-l,3,2-dioxaborolanes
.
.
567
VIH.
Oxybis(acetoxychloroborane)
.....
567
A.
Methods
of
Preparation
.....
567
1.
From
boron
trichloride
and
acetic
acid
esters
.
567
2.
Prom
boron
trichloride
and
acetic
acid
or
anhydride
.......
567
XXIV
Contents
B.
Reactions
......
.
568
1.
Pyrolysis
.....
.
568
2.
With
acetic
acid
....
.
568
IX.
Analytical
......
.
568
A.
Fluorine
Derivatives
....
.
568
B.
Chlorine
Derivatives
....
.
569
X.
Physical
Constants
.....
.
571
XI.
References
......
.
586
IB.
Siloxy
Derivatives
......
.
590
I.
Introduction
......
.
590
II.
Historical
......
.
590
III.
Properties
......
.
591
IV.
Silyl
Orthoborates
.....
.
591
A.
Methods
of
Preparation
.
591
1.
From
boric
acid
....
.
591
a.
And
silanols
....
.
591
b.
And
alkoxyalkysilanes
.
592
c.
And
alkylchlorosilanes
.
593
d.
And
trialkylsilanes
.
.
594
e.
And
dimethylpolysiloxanes
.
595
2.
From
boric
oxide
.
595
a.
And
silanols
....
.
595
b.
And
alkoxytrialkylsilanes
.
.
595
c.
And
hexaalkyldisiloxanes
.
.
595
3.
From
boron
halides
.
596
a.
And
silanols
....
.
596
b.
And
alkoxydialkylhalosilanes
or
alkoxy-
trihalosilanes
....
.
596
c.
And
eyclosiloxanes
.
.
596
4.
From
trialkoxyboranes
.
.
597
a.
And
silanols
....
.
597
b.
And
trialkylhalosilanes
.
597
c.
And
diacetoxydialkylsilanes
.
598
5.
From
triacetoxyborane
.
.
599
a.
And
dialkoxydialkylsilanes
.
599
b.
And
methyl
silicate
.
.
599
6.
From
tris(alkylamino)boranes
.
600
7.
From
other
tris(trialkylsiloxy)boranes
.
600
8.
From
dialkylhalosiloxydihaloboranes
.
600
9.
From
bis(trialkylsiloxy)haloboranes
.
601
B.
Reactions
......
.
601
1.
Hydrolysis
.....
.
601
2.
Thermal
stability
....
.
602
3.
With
hydrogen
halides
.
.
603
Contents
xxv
4.
With
boric
oxide
......
603
5.
With
trialkylsilanols
.....
603
V.
Silyl
Metaborates
.......
603
A.
Methods
of
Preparation
.....
603
B.
Reactions
........
603
VI.
Analytical
........
604
VII.
Physical
Constants
.......
605
VIII.
References
........
608
14.
Coordination
Compounds
Derived
from
Monohydric
Alcohols
and
Phenols
.........
609
I.
Introduction
........
609
II.
Historical
........
610
III.
Properties
........
610
IV.
Methods
of
Preparation
......
612
A.
Prom
Trialkoxyboranes
.....
612
1.
And
metal
alkoxides
.....
612
2.
And
sodium
hydride
.....
614
B.
From
Borohydrides
......
614
1.
And
alcohols
......
614
2.
And
aldehydes
and
ketones
.
.
.
.614
C.
Prom
Sodium
Trimethoxyhydroborate
.
.
.615
1.
Disproportionation
.....
615
2.
And
alcohols
......
615
D.
Prom
Alkali
Borates
and
Methanol
.
.
.
615
E.
From
Other
Tetraalkoxyborates
....
615
1.
Exchange
of
cations
.....
615
2.
Exchange
of
alkoxyl
ligands
....
616
V.
Reactions
........
617
A.
Hydrolysis
.
.
.
.
.
.
.617
B.
Thermal
Stability
......
617
C.
With
Hydridic
Materials
.
.
.
.
.619
D.
With
Carbon
Dioxide
......
620
E.
Miscellaneous
.......
620
VI.
Analytical
........
620
VII.
Physical
Constants
.
.
.
.
.
.
.621
VIII.
References........624
15.
Coordination
Compounds
Derived
from
Polyhydric
Alcohols
and
Phenols
.........
626
I.
Introduction
........
626
II.
Historical
........
630
III.
Bisdiolborates
........
631
A.
Properties
........
631
1.
General
.......
631
2.
Asymmetry
.......
636
XXVI
Contents
B.
Methods
of
Preparation
of
Acids
....
636
1.
By
esterification
of
boric
acid
or
equivalent
.
636
2.
By
pyrolysis
of
bisdiolborate
salts
.
.
•
638
3.
From
dioldialkoxyborates
....
639
4.
From
2-hydroxy-
1,3.2-dioxaborolanes
.
.
639
C.
Methods
of
Preparation
of
Salts
....
640
1.
By
removal
of
water
from
mixture
of
diol,
boric
acid
and
base
......
640
2.
By
crystallization
from
an
aqueous
solution
of
diol,
boric
acid
and
base
....
641
3.
From
hydrogen
bisdiolborates
.
.
.
642
4.
From
dioldialkoxyborates
....
643
5.
By
hydrolysis
of
a
triglycol
biborate
in
the
presence
of
a
base
......
644
6.
By
reaction
of
tropolones
and
2-alkoxy-l,3,2-
dioxaboroles
......
644
D.
Reactions
of
Acids
.
.
.
.
•
•
645
E.
Reactions
of
Salts
...
.
.
.
.
645
1.
Hydrolysis
......
645
2.
Alcoholysis
.......
646
3.
Thermal
stability
......
647
IV.
Bissugarborates
.......
648
V.
Dioldialkoxyborates
.......
650
A.
Methods
of
Preparation
of
Acids
....
650
B.
Methods
of
Preparation
of
Salts
....
650
1.
By
crystallization
from
an
aqueous
solution
of
diol,
boric
acid
and
base
....
650
2.
From
bisdiolborates
.....
650
3.
From
tri-(3-hydroxyalkoxyboranes
.
.
.
651
C.
Reactions
........
651
1.
Conversion
to
bisdiolborate
salts
and
acids
.
651
2.
Hydrolysis
and
alcoholysis
....
651
VI.
Dihydroxydiolborates
......
652
A.
Properties
........
652
B.
Methods
of
Preparation
of
Acids
....
652
C.
Methods
of
Preparation
of
Salts
....
656
1.
From
an
aqueous
solution
of
diol,
boric
acid
and
base
........
656
2.
From
dihydroxydiolborate
acids
.
.
658
D.
Reactions
of
Acids
......
658
1.
With
hydroxylic
solvents
....
658
2.
Conversion
to
salts
.....
659
3.
Dehydration
......
659
E.
Reactions
of
Salts
......
659
VII.
Hydroxytriolborates
......
659
Contents
xxvii
VIII.
Stereochemical
Considerations
.....
661
A.
Introduction
.......
661
B.
Conductivity
Considerations
....
661
1.
1,2-Diols
.......
661
2.
1,3-
and
1,4-Diols.....666
3.
Triols,
tetrols,
pentitols
and
hexitols
.
.
667
4.
Alicyclic
diols
......
667
5.
Aromatic
derivatives
.....
671
6.
Sugars
.......
671
C.
Ionophoretic
Mobility
Considerations
.
.
.
675
1.
Introduction
......
675
2.
Acyclic
polyols
......
681
3.
Alicyclic
polyols
......
682
4.
Sugars
.......
684
D.
Optical
Rotation
Considerations
....
685
E.
Acidity
Considerations
.....
689
1.
Introduction
......
689
2.
Acyclic
polyols
......
691
3.
Alicyclic
polyols
......
693
4.
Aromatic
derivatives
.....
695
5.
Sugars
.......
695
F.
Ion-Exchange
Resins
.....
696
IX.
Analytical
........
697
X.
Physical
Constants
......
698
XI.
References
........
727
16.
Coordination
Compounds
Derived
from
Hydroxy
Acids
and
Dibasic
Acids
.........
732
I.
Introduction
........
732
II.
Historical
........
733
III.
Properties
........
733
A.
General
........
733
B.
Stereochemistry.......
733
IV.
Hydroxy
Acid
Derivatives
.....
736
A.
Methods
of
Preparation
.....
736
1.
Salts
with
1:1
mole
ratio
hydroxy
acid
to
boron
736
2.
Acids
with
2:1
mole
ratio
hydroxy
acid
to
boron
738
a.
From
hydroxy
acids
and
boric
acid
.
.
738
b.
From
hydroxy
acids
and
trialkoxyboranes
.
738
c.
From
acetoxyborane
derivatives
.
.
738
d.
From
salts
with
2:1
mole
ratio
hydroxy
acid
to
boron
......
739
e.
From
other
sources
.....
739
3.
Salts
with
2:1
mole
ratio
hydroxy
acid
to
boron
739
a.
From
hydroxy
acids,
boric
acid
and
base
.
739
b.
From
hydroxy
acid
salts
and
boric
acid
.
743
Contents
xx
viii
c.
From
acids
with
2:1
mole
ratio
hydroxy
acid
to
boron
.......
743
d.
From
other
salts
with
2:1
mole
ratio
hydroxy
acid
to
boron
......
743
4.
Salts
with
2:3
mole
ratio
hydroxy
acid
to
boron
743
B.
Reactions
........
744
1.
Hydrolysis
.......
744
2.
Alcoholysis
.......
745
3.
Pyrolysis
.......
745
4.
With
hydrogen
sulfide
.....
746
V.
Dibasic
Acid
Derivatives
......
746
A.
Methods
of
Preparation
.....
746
B.
Reactions
........
747
VI.
Stereochemical
Considerations
.....
747
A.
Introduction
.......
747
B.
Conductivity
Considerations
....
748
1.
Hydroxy
acids
.
.
.
.
.748
2.
Keto
acids
.......
756
3.
Dibasic
acids
......
757
C.
Optical
Rotation
Considerations
.
.
.
.758
D.
Acidity
and
Equilibrium
Considerations
.
.759
VII.
Analytical........761
VIII.
Physical
Constants
.
.
.
.
.
.
.762
IX.
References
........
773
17.
Tetra(alkoxyhydro)-
and
Tetra(acyloxyhydro)borates
775
I.
Introduction
........
775
II.
Historical
........
775
III.
Properties
........
778
IV.
Trialkoxyhydroborates
......
778
A.
Methods
of
Preparation
.....
778
B.
Reactions
........
779
1.
Hydrolysis
.......
779
2.
Alcoholysis
.
.
.
.
.
.780
3.
Disproportionation
.
.
.781
4.
With
hydridic
materials
....
781
5.
With
trimethoxyborane
....
782
6.
With
trimethoxyboroxine
....
782
7.
With
triethylborane
.....
782
8.
With
boron
trihalides
.....
783
9.
With
chloroborazines
.
.
.784
10.
With
hydrogen
chloride
.
.784
11.
With
silicon
tetrachloride
.
.785
12.
With
carbon
dioxide
.....
785
13.
Reduction
of
organic
compounds
.785
14.
Reduction
of
inorganic
species
.
.
787
Contents
xxix
V.
Dialkoxydihydroborates
.
.
.
.
.
.787
VI.
Alkoxytrihydroborates
.
.
.
.
.
.788
A.
Methods
of
Preparation
.
.
.
.
.788
1.
From
diborane
and
metal
alkoxides
.
.
788
2.
From
sodium
borohydride
and
phenols
.
.
788
B.
Reactions
........
788
VII.
Tetra(acyloxyhydro)borates
.....
788
VIII.
Analytical
........
790
IX.
Physical
Constants
.
.
.
.
.
.
.790
X.
References
........
791
18.
Coordination
Compounds
Derived
from
Boron
Trifluoride
and
Alcohols,
Phenols
or
Acids
.......
793
I.
Introduction
........
793
II.
Historical
........
794
III.
Properties
........
794
A.
General
........
794
B.
Structure
........
795
IV.
Methods
of
Preparation
......
796
A.
From
Direct
Reaction
of
Boron
Trifluoride
with
Alcohols,
Phenols
or
Acids
.
.
.
.
.796
B.
From
Boron
Trifluoride
and
Metal
Alkoxides
.
797
C.
From
Boron
Trifluoride
and
Carboxylic
Acid
Anhydrides
.......
797
D.
From
Alkoxydifluoroboranes
....
798
E.
From
Dihydroxyfluoboric
Acid
and
Acetyl
Chloride
798
F.
From
1:1
Boron
Trifluoride-Carboxylic
Acid
Com¬
plexes
........
798
V.
Reactions
........
798
A.
Thermal
Stability
.
.
.
.
.
.798
1.
Alcohol
complexes
.
.
.
.
.798
2.
Acid
complexes
.
.
.
.
.
.799
B.
Hydrolysis
.......
800
C.
With
Alcohols.......800
D.
With
Ammonia
and
Amines
....
800
E.
With
Olefins
.......
801
F.
With
Alkali
Halides
......
801
G.
With
Boron
Trifluoride
.....
801
H.
With
Sodium
.......
801
I.
With
Hydroxides
and
Oxides
....
801
J.
Attempted
Reaction
with
Sodium
Methoxide
.
801
VI.
Analytical
........
802
VII.
Physical
Constants
.......
803
VIII.
References
........
809
XXX
Contents
19.
Boronium
Salts
.........
811
I.
Introduction
and
Historical
.
.
.
.
.811
II.
Properties
........
812
III.
Methods
of
Preparation
......
812
A.
From
Boron
Trichloride
and
[3-Diketones
.
.
812
B.
From
Boronium
Chlorides
and
Iodides
.
.
.
813
C.
From
Hydroxyketones
.....
814
IV.
Reactions
........
814
V.
Analytical
........
814
VI.
Physical
Constants
.
.
.
.
.815
VII.
References
........
816
20.
Boron-Sulfur
Compounds
.......
817
I.
Introduction
........
817
II.
Historical
.
.
.
818
III.
Properties
........
818
A.
General
........
818
B.
Structure
........
819
TV.
Trialkyl-
and
Triarylthioboranes
....
821
A.
Methods
of
Preparation
.....
821
1.
From
mercaptans
......
821
a.
And
boron
trihalides
.....
821
b.
And
boron
sulfide
.....
822
c.
And
dialkylthioboranes
....
822
d.
And
amine
boranes
.....
822
e.
And
tris(alkylamino)boranes
.
.
.
822
f.
And
alkylthiodiboranes
....
822
2.
From
mercaptides
and
boron
trihalides
.
.
823
3.
From
alkylthiohaloboranes
and
hydrogen
sulfide
823
4.
From
trialkoxyboranes
and
phosphorus
penta-
sulfide
.......
824
6.
From
triphenylthioaluminum
and
potassium
fluoborate
.......
824
6.
By
disproportionation
of
methylthioborane
.
824
7.
By
disproportionation
of
alkyl(alkylthio)boranes
824
8.
Attempted
preparations
....
825
B.
Reactions
........
825
1.
Hydrolysis
.......
825
2.
Alcoholysis
.......
825
3.
With
amines
......
826
4.
With
boron
trihalides
.....
826
5.
With
alkoxy(alkyl)boranes
....
826
6.
With
thiometaboric
acid
.
.
.
.
826
7.
With
trialkylboranes
.....
827
Contents
XXXI
V.
Alkylthioboranes
.......
827
A.
Methods
of
Preparation
.....
827
B.
Reactions
........
828
1.
Thermal
.......
828
2.
Hydrolysis
.......
829
3.
With
amines
......
829
4.
With
diborane
......
829
5.
With
mercaptans
.
.
.
.
.
.
829
VI.
Alkylthiohaloboranes
......
829
A.
Methods
of
Preparation
.....
829
1.
From
mercaptans
and
boron
trihalides
.
.
829
2.
From
trialkylthioboranes
and
boron
trihalides
.
830
B.
Reactions
........
830
VII.
2-Halo-1,3,2-dithiaborolanes
.....
830
VIII.
2-Alkylthio-l,3,2-dioxaborolanes
....
831
A.
Methods
of
Preparation
.....
831
B.
Reactions
........
831
IX.
Trialkoxyborthiins
.......
832
A.
Methods
of
Preparation
.....
832
B.
Reactions
........
833
X.
Trialkylthioborthiins
......
833
A.
Methods
of
Preparation
.....
833
B.
Reactions
........
834
XI.
Alkylthiotrihaloborates
......
834
XII.
Analytical
........
834
Xin.
Physical
Constants
.......
835
XIV.
References
........
837
21.
Hydrolytic
Stability
........
840
I.
Introduction
.
.
.
.
.
•
•
840
II.
Historical
.
.
.
.
•
•
•
840
III.
Orthoborates
........
840
A.
General
Background
......
840
B.
Useful
Aspects
of
Instability
....
841
C.
Mechanism
of
the
Hydrolysis
....
841
D.
Partial
Hydrolysis
......
842
1.
Trialkoxy-
and
triaryloxyboranes
.
.
.
842
2.
Glycol
biborates
.
.
.
.
.
843
3.
Unsymmetrical
orthoborates
....
844
E.
Rates
of
Hydrolysis
.
.
.
.
.
845
1.
Steric
factors
......
845
a.
Effect
of
base
......
847
b.
Conclusions
......
849
2.
Electronic
factors
......
850
F.
Equilibrium
Constants
.....
852
xxxii
Contents
IV.
Hindered
Phenolic
Borates
.....
852
V.
Trialkanolamine
Borates
......
855
A.
Triethanolamine
Borate
.....
855
B.
Triisopropanolamine
Borate
....
857
C.
Tri-n-propanolamine
Borate
....
863
VI.
2-Hydroxy-1,3,2-dioxaborolanes
and
Borinanes
and
Their
Salts
and
Anhydrides
....
863
VII.
Metaborates
........
866
VIII.
References
........
868
Appendix
A
........
871
I.
Infrared
Assignments
.
.
.
.
.
.871
II.
References
........
882
Appendix
B
........
884
I.
Bond
Energies
and
Bond
Distances
....
884
II.
References
.
.
.
.
.
.—
.
.
884
Appendix
C
.
885
I.
Heats
of
Formation
.......
885
II.
References
........
885
Author
Index
.........
887
Subject
Index
.........
929
|
| any_adam_object | 1 |
| author | Steinberg, Howard |
| author_facet | Steinberg, Howard |
| author_role | aut |
| author_sort | Steinberg, Howard |
| author_variant | h s hs |
| building | Verbundindex |
| bvnumber | BV009379762 |
| ctrlnum | (OCoLC)310030164 (DE-599)BVBBV009379762 |
| format | Book |
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| id | DE-604.BV009379762 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T17:35:19Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-006224786 |
| oclc_num | 310030164 |
| open_access_boolean | |
| owner | DE-29T DE-20 DE-188 DE-11 |
| owner_facet | DE-29T DE-20 DE-188 DE-11 |
| physical | XXXII, 950 S. Ill. |
| psigel | HUB-ZB011201111 |
| publishDate | 1964 |
| publishDateSearch | 1964 |
| publishDateSort | 1964 |
| publisher | Interscience Publ. |
| record_format | marc |
| spelling | Steinberg, Howard Verfasser aut Organoboron chemistry 1 Boron-oxygen and boron-sulfur compounds Howard Steinberg New York [u.a.] Interscience Publ. 1964 XXXII, 950 S. Ill. txt rdacontent n rdamedia nc rdacarrier (DE-604)BV009379761 1 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006224786&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Steinberg, Howard Organoboron chemistry |
| title | Organoboron chemistry |
| title_auth | Organoboron chemistry |
| title_exact_search | Organoboron chemistry |
| title_full | Organoboron chemistry 1 Boron-oxygen and boron-sulfur compounds Howard Steinberg |
| title_fullStr | Organoboron chemistry 1 Boron-oxygen and boron-sulfur compounds Howard Steinberg |
| title_full_unstemmed | Organoboron chemistry 1 Boron-oxygen and boron-sulfur compounds Howard Steinberg |
| title_short | Organoboron chemistry |
| title_sort | organoboron chemistry boron oxygen and boron sulfur compounds |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006224786&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV009379761 |
| work_keys_str_mv | AT steinberghoward organoboronchemistry1 |