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The reaction of tris(trimethylsilyl)silane with acid chlorides

✍ Scribed by M. Ballestri; C. Chatgilialoglu; N. Cardi; A. Sommazzi

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
268 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

Tris(trimethylsilyl)silane, in contrast with tributyltin hydride, reduces acid chlorides to the corresponding decarboxylated hydrocarbons via a free radical mechanism. This methodology could be a viable alternative to Barton's decarboxylation reaction. Tributyltin hydride reacts spontaneously at ambient temperature with acid chlorides, RC(O)Cl, to form BugSnCl, RCHO, RC(O)OCH,R and a number of minor products .I It is well-known that the majority of reactions involving tributyltin hydride occur via free radicals.2 Ingold and coworkers3 have shown, in disagreement with earlier conclusions4 that free radicals are not involved in such a spontaneous reaction. When

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