Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

Hydrosilation In The Synthesis Of Organosilanes

R. N. Meals
Published 1966 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy
Share
INTRODUCTION The hydrosilation reactions, i.e. the addition of silanes to olefins ( equation 1) emerged from about six separate laboratories in the United States15 between 1945 and 1947. 1 YCH2CH2SiX3 YCH=CH2 + HSiX3 iCatalyst ·~ YCH-CH3 (1) I SiX3 A silanesuch as trichlorosilane adds to an olefin such as ethylene to give an organosilicon compound. The substituents X and Y can be varied rather widely, e.g. alkyl, aryl, halogen, alkoxy, and acyloxy for either X or Y. The reaction is very versatile. But changes in reaction rateandin the course of the reaction depend upon the substituents X and Y and the catalyst. The reaction is very complex and it is not a simple matter to make really effective use of it. The usefulness ofthe reaction is limited by a number ofthings. There are some side reactions, including polymerization and isomerization of the olefin, and these cannot always be controlled. We do not know how to make all possible combinations of silanes and olefins react, let alone to make at will the upper or lower type product of equation (1). The silane we need may not be readily available. In the laboratory this is an inconvenience; on a larger scale it can make hydrosilation impracticable. There are other ways to synthesize silanes, and sometimes Grignard processes are attractive when the alternative involves making a silicon-hydrogen compound first. There are only a handful of hydrosilanes that we can get by direct means, for example as products or by-products of the direct process, and fewer stillthat are really abundant. Hydrosilation is potentially useful for doing things besides the simple reaction illustrated in equation (1). A number of products have been obtained by the reaction of silanes with olefins. Table 1 shows the products obtained when: (i) the silane is a monomer, and the olefinic group is attached to silicon, compounds with two silicon atoms are obtained; (ii) two (or more) silicon atoms are put on unsaturated polymers; (iii) substituted siloxanes are made by different routes; (iv) a siloxane containing SiH is alkylated to an alkylsiloxane. Silicone organic co-polymers can be made from unsaturated organic polymers. Siloxane polymers containing SiH combine with those containing vinyl groups to give cross-linked or cured
This paper references
10.1021/JA01203A039
Alkylation of Hydrochlorosilanes
C. A. Burkhard (1947)
10.1021/JA01552A072
The Stereochemistry of the Addition of Silicochloroform to Acetylenes
R. A. Benkeser (1958)
10.1021/JA01079A004
Homogeneous Catalysis. II. The Mechanism of the Hydrosilation of Olefins Catalyzed by Group VIII Metal Complexes1
A. Chalk (1965)
10.1021/JO01016A004
Electrolytic Reductive Coupling. VIII.1 Utilization and a New Preparation of α-Methyleneglutaronitrile
M. M. Baizer (1965)
10.1021/JA01465A061
SILICON HYDRIDE-OLEFIN ADDITIONS
B. A. Bluestein (1961)
10.1246/BCSJ.29.322
Cyanoethylation of Trichlorosilane. II. α-Addition
S. Nozakura (1956)
10.1021/JO01053A072
Preparation of β-Cyanoethyltrichlorosilane Using Silylamine Catalysts
R. A. Pike (1962)
10.1021/JO01053A071
Base-Catalyzed Additions of Trichlorosilane to Hydrocarbon Olefins
R. A. Pike (1962)
10.1351/pac196613010133
Silane addition reactions - their synthetic utility and mechanism
R. A. Benkeser (1966)
10.1021/JA01499A031
The Addition of Silicon Hydrides to Olefinic Double Bonds. Part V. The Addition to Allyl and Methallyl Chlorides
J. Ryan (1960)
10.1021/JA01569A023
The Addition of Chloro- and Ethoxysilanes to Vinyl and Allyl Monomers1,2
L. Goodman (1957)
10.1021/JA00897A017
Anionic Activation of C-H Bonds in Olefins. VI. Intramolecular Nature and Kinetic Isotope Effect of Base-Catalyzed Olefin Isomerization
S. Bank (1963)
10.1021/JA01182A014
A new synthesis of organosilicon compounds.
E. W. Pietrusza (1948)
10.1039/JR9640001548
307. Organosilicon compounds. Part XXVII. The reaction between trichlorosilane and 4-chlorophenylbut-1-enes
R. Bott (1964)
10.1021/JO01032A009
The Addition of Silicon Hydrides to Olefinic Double Bonds. X. Addition to Phenylalkenes. The Nuclear Magnetic Resonance Proton Spectra of (Phenylalkyl)silanes
M. C. Musolf (1964)
10.1021/JA01059A030
The Addition of Silicon Hydrides to Olefinic Double Bonds. VIII. The Addition of Trichlorosilane-d
J. Ryan (1964)
37 J
York (1956)
10.1070/RC1962V031N07ABEH001301
ORGANOSILICON COMPOUNDS CONTAINING A CYANO-GROUP
V. Vdovin (1962)
10.1021/JA01063A024
Homogeneous Catalysis. I. Double Bond Migration in n-Olefins, Catalyzed by Group VIII Metal Complexes
J. Harrod (1964)
10.1021/JA01514A022
The Cyanoethylation of Phosphine and Phenylphosphine
M. Rauhut (1959)
10.1021/JO01085A611
Notes- Cyanoethylation of Trichlorosilane
J. Saam (1959)
10.1021/JA01482A022
The Stereochemistry of the Addition of Silicochloroform to Acetylenes. A Comparison of Catalyst Systems
R. A. Benkeser (1961)
10.1021/JA01540A058
γ-Ray Initiated Reactions. II. The Addition of Silicon Hydrides to Alkenes1
A. M. El-Abbady (1958)
10.1021/JA01203A010
Mechanism of the Alkaline Cleavage of Silicon—Hydrogen Bonds: Temperature Coefficients of the Rate of Cleavage of Several Trialkylsilanes
F. P. Price (1947)
10.1021/JO01028A057
Definition of “Inductive” Substituent Constants
M. Charton (1964)
10.1021/JA01193A508
PEROXIDE-CATALYZED ADDITION OF TRICHLOROSILANE TO 1-OCTENE
L. H. Sommer (1947)
Steric Effects in Organic Chemistry, p. 556ff
R. W. Taft (1961)
10.1021/JA01203A512
THE REACTION OF OLEFINS AND CHLOROHYDROSILANES
A. J. Barry (1947)
10.1021/JO01027A006
The Addition of Silicon Hydrides to Olefinic Double Bonds. IX. Addition of sym-Tetramethyldisiloxane to Hexene-1, -2, and -3
H. M. Bank (1964)
10.1021/JA01568A028
Aliphatic Organo-functional Siloxanes. V. Synthesis of Monomers by Platinum-catalyzed Addition of Methyldichlorosilane to Unsaturated Esters and Nitriles1
L. H. Sommer (1957)
10.1021/JO01094A626
Notes- Addition of Silicon Hydrides to Olefinic Double Bonds. IV. The Addition to Styrene and α-Methylstyrene
John Ryan (1959)
10.1021/JA01467A024
The Addition of Silicon Hydrides to Olefinic Double Bonds. Part VI. Addition to Branched Olefins
J. Saam (1961)
10.1021/JA01591A068
The Addition of Silicon Hydrides to Olefinic Double Bonds. Part I. The Use of Phenylsilane, Diphenylsilane, Phenylmethylsilane, Amylsilane and Tribromosilane
J. L. Speier (1956)
10.1021/JA01548A073
The Addition of Silicon Hydrides to Olefinic Double Bonds. Part III. The Addition to Non-terminal Olefins in the Presence of Chloroplatinic Acid
J. Saam (1958)
10.1021/JA01083A034
Dicobalt Octacarbonyl as a Catalyst for Hydrosilation of Olefins
J. Harrod (1965)
10.1021/JA01469A032
Reversibility in the Reaction of Phosphinyl Radicals with Olefins
Joseph Pellon (1961)
10.1021/JA01561A054
The Addition of Silicon Hydrides to Olefinic Double Bonds. Part II. The Use of Group VIII Metal Catalysts
J. L. Speier (1957)
10.1021/JO01115A614
Notes - The Addition of Trichlorosilane to Pentene-1 with Peroxide Initiators
J. L. Speier (1956)



This paper is referenced by
10.1016/0009-2509(93)80028-O
The preparation of colloidal particles having (post-grafted) terminally-attached polymer chains
B. Vincent (1993)
10.1007/BF00702499
Synthesis of siloxanes containing reactive side chains
S. K. Duplock (1991)
10.1016/J.JLUMIN.2011.10.027
Structural and photophysical properties of anthracenyl and carbazolyl groups in silicone-based polymers
Raquel Aparecida Domingues (2012)
10.1002/BSCB.19911000311
Enantioselektive Katalyse, 63 [1] Optisch Aktive Phosphine Aus Dicarbonsäuren Und Ihr Einsatz in Der Enantioselektiven Hydrierung
H. Brunner (2010)
10.1007/978-94-010-1199-0_3
Asymmetric Hydrosilylation by Means of Homogeneous Catalysts with Chiral Ligands
I. Ojima (1977)
10.1002/JBM.820160402
Rheological studies of the polymerization of elastomeric impression materials. I. Network structure of the set state.
W. D. Cook (1982)
10.1111/J.1365-2842.1988.TB00202.X
Physical properties of addition silicones as a function of composition.
J. R. Williams (1988)
10.1016/0032-3861(87)90326-0
Thermally reactive oligomers of aromatic poly(ether sulphone) containing poly(dimethylsiloxane): 1. Synthesis and characterization
B. Auman (1987)
10.1016/0032-3861(87)90460-5
Alternating block copolymers of aromatic poly(ether sulphone) and poly(dimethylsiloxane) by hydrosilylation
B. Auman (1987)
10.1039/B406341D
Polysiloxane-bound ligand accelerated catalysis: a modular approach to heterogeneous and homogeneous macromolecular asymmetric dihydroxylation ligands.
Michael S. DeClue (2004)
10.1016/S0022-328X(00)87493-8
Hydrosiloxane additions and isomerizations of 2- and 1-propenyl benzyl ethers
C. L. Schilling (1971)
Polybutadiene Graft Copolymers as Coupling Agents in Rubber Compounding
Nicole Swanson (2016)
10.1002/CHIN.198445382
Stereochemistry at Silicon
R. Corriu (1984)
10.2172/1048493
Development of Chemiresponsive Sensors for Detection of Common Homemade Explosives
Christopher M. Brotherton (2012)
10.1007/3-540-06714-0_9
The chemistry of silicon-transition-metal compounds
F. Hoefler (1974)
10.1016/S0022-328X(00)81636-8
Hydrosilane addition of perfluorophenylsilanes to some unsaturated systems
T. Brennan (1969)
10.1002/PI.4990280208
The synthesis and characterization of poly(ethylene oxide)-b-poly-(dimethylsiloxane) diblock copolymers
Z. Király (1992)
10.1002/HLCA.19710540510
Tetrakis‐triphenylphosphin‐platin(0), ein Katalysator zur selektiven Hydrosilylierung
W. Fink (1971)
Semantic Scholar Logo Some data provided by SemanticScholar