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Homolytic Substitution Reaction at a Silicon Atom
Author(s) -
Kulicke Klaus.,
Chatgilialoglu Chryss Stomos,
Kopping Birgit,
Iese Bernd
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750327
Subject(s) - chemistry , homolysis , alkyl , trimethylsilyl , silane , medicinal chemistry , substitution (logic) , photochemistry , hydrogen atom , free radical reaction , radical cyclization , substitution reaction , radical , organic chemistry , computer science , programming language
Tris(trimethylsilyl)silane ( 2 ) is an efficient hydrosilylating agent of 1,6‐dienes 1 operating via a free‐radical chain mechanism. The intermediate alkyl radical 3 attacks the second olefinic bond of the diene 1 and forms cyclopentylalkyl radical 4 . Using a low concentration of the hydrogen donor 2 , a radical substitution reaction at the Si‐center of cis ‐ 4 occurs and yields the bicyclic silane 6 . The rate of this homolytic substitution at the Si‐atom is 2.4 · 10 5 s ‐1 (80°).