A very fast [1,4] carbon-to-oxygen silicon migration-rearrangement leading to O-silylated cinnamyl alcohols occurs when the carbanion generated from sulfone 1 is reacted with carbonyl compounds. The mandatory role of the adjacent phenyl ring in this process is demonstrated when compared to the behaviour of the corresponding unsubstituted sulfone 3
Phenyl group acceleration of [1,4]carbon-to-oxygen silicon-mediated elimination-rearrangement in b-silyl sulfones. Synthesis of O-silylated cinnamyl alcohols / S. Menichetti; C. J. M. Stirling. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1. - ISSN 1472-7781. - STAMPA. - -:(2002), pp. 28-30. [10.1039/b109805e]
Phenyl group acceleration of [1,4]carbon-to-oxygen silicon-mediated elimination-rearrangement in b-silyl sulfones. Synthesis of O-silylated cinnamyl alcohols
MENICHETTI, STEFANO;
2002
Abstract
A very fast [1,4] carbon-to-oxygen silicon migration-rearrangement leading to O-silylated cinnamyl alcohols occurs when the carbanion generated from sulfone 1 is reacted with carbonyl compounds. The mandatory role of the adjacent phenyl ring in this process is demonstrated when compared to the behaviour of the corresponding unsubstituted sulfone 3
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