Open AccessTributyl[2-(trimethylsilyl)-prop-2-enyl]stannane: A Highly Efficient Reagent for the Allylation of Radicals
Author(s) -
Philippe Renaud,
Michèle Gerster,
M. Ribezzo
Publication year - 1994
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.1994.366
Subject(s) - stannane , chemistry , radical , trimethylsilyl , substituent , medicinal chemistry , electrophile , nucleophile , reagent , photochemistry , organic chemistry , catalysis
Allylation rates of radicals with tributyl[2-(trimethylsilyl)prop-2-enyl]stannane (2) have been compared with the ones of the (prop-2-enyl)stannane (3) and [2-(methyl)-prop-2-enyl]stannane (4). The Me3Si substituent showed a rate-accelerating effect (4.2:1 to 6.5:1) relative to the H-atom and the Me group for nucleophilic radicals. With electrophilic radicals, the Me group has a better rate accelerating effect than the Me3Si group. All these results can be understood by postulating a partially polarized transition state. The 1-substituted vinylsilanes which are produced by radical allylation with 2 have been converted by protiodesilylation and ozonolysis to alkenes and α-hydroxy ketones.