Advanced

The effect of oxygen on the regioselectivity in the rhodium catalysed hydrosilylation of 1,3-dienes

Gustafsson, Magnus LU and Frejd, Torbjörn LU (2002) In Perkin Transactions 1 p.102-107
Abstract
The regioselectivity of the hydrosilylation of substituted 1,3-dienes catalysed by several rhodium complexes in the presence and absence of oxygen was studied. In addition to the already known accelerating effect, the presence of oxygen strongly affected the product distribution. For 2-substituted 1,3-dienes in the presence of oxygen the regioselectivity was in the range of 1 : 6 to 1 : 10 in favour of the head-product, while the absence of oxygen changed the ratios to 1 : 1 to 3 : 1 in fa our of the tail-product. When HSiPh3 was used in the presence of oxygen a single isomer was isolated in 87% yield, while in the absence of oxygen a mixture of products was produced. Control experiments indicated that a heterogeneous/colloidal catalytic... (More)
The regioselectivity of the hydrosilylation of substituted 1,3-dienes catalysed by several rhodium complexes in the presence and absence of oxygen was studied. In addition to the already known accelerating effect, the presence of oxygen strongly affected the product distribution. For 2-substituted 1,3-dienes in the presence of oxygen the regioselectivity was in the range of 1 : 6 to 1 : 10 in favour of the head-product, while the absence of oxygen changed the ratios to 1 : 1 to 3 : 1 in fa our of the tail-product. When HSiPh3 was used in the presence of oxygen a single isomer was isolated in 87% yield, while in the absence of oxygen a mixture of products was produced. Control experiments indicated that a heterogeneous/colloidal catalytic system may be responsible for the preferred head-product formation. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Perkin Transactions 1
issue
1
pages
102 - 107
publisher
Royal Society of Chemistry
external identifiers
  • wos:000172813200014
  • scopus:0036006965
ISSN
1472-7781
DOI
10.1039/b106143g
language
English
LU publication?
yes
id
3a9d3427-387a-4c62-8994-5970c18e6e2f (old id 347664)
date added to LUP
2007-08-22 14:31:04
date last changed
2017-01-01 06:54:35
@article{3a9d3427-387a-4c62-8994-5970c18e6e2f,
  abstract     = {The regioselectivity of the hydrosilylation of substituted 1,3-dienes catalysed by several rhodium complexes in the presence and absence of oxygen was studied. In addition to the already known accelerating effect, the presence of oxygen strongly affected the product distribution. For 2-substituted 1,3-dienes in the presence of oxygen the regioselectivity was in the range of 1 : 6 to 1 : 10 in favour of the head-product, while the absence of oxygen changed the ratios to 1 : 1 to 3 : 1 in fa our of the tail-product. When HSiPh3 was used in the presence of oxygen a single isomer was isolated in 87% yield, while in the absence of oxygen a mixture of products was produced. Control experiments indicated that a heterogeneous/colloidal catalytic system may be responsible for the preferred head-product formation.},
  author       = {Gustafsson, Magnus and Frejd, Torbjörn},
  issn         = {1472-7781},
  language     = {eng},
  number       = {1},
  pages        = {102--107},
  publisher    = {Royal Society of Chemistry},
  series       = {Perkin Transactions 1},
  title        = {The effect of oxygen on the regioselectivity in the rhodium catalysed hydrosilylation of 1,3-dienes},
  url          = {http://dx.doi.org/10.1039/b106143g},
  year         = {2002},
}