Ozone Oxidation of Silylalkene: Mechanistic Study and Application for the Synthesis of Silacarboxylic Acid Derivatives

The Journal of Organic Chemistry
Kazunobu IgawaKatsuhiko Tomooka

Abstract

The addition-type ozone oxidation of silylalkenes is a highly efficient reaction to provide synthetically versatile α-silylperoxy carbonyl compounds. To gain insight into the reaction mechanism, we performed a computational study, which revealed that the reaction proceeds via [1,2]-Brook rearrangement-type silyl migration of primary ozonide. In sharp contrast to the addition-type reactions, the ozone oxidation of α-alkoxysilylalkenes proceeds in a cleavage-type manner to afford excellent yields of silacarboxylic acid esters via the 1,3-cycloelimination of primary ozonide prior to 1,2-silyl migration.

References

Oct 8, 2005·Organic & Biomolecular Chemistry·James C AndersonMatthew Whiting
Nov 29, 2005·Angewandte Chemie·Kazunobu Igawa, Katsuhiko Tomooka
Dec 24, 2009·Angewandte Chemie·Kazunobu IgawaKatsuhiko Tomooka
Dec 7, 2011·Journal of the American Chemical Society·Yuuya KawasakiKatsuhiko Tomooka
Nov 9, 2012·Angewandte Chemie·Kazunobu IgawaKatsuhiko Tomooka
Jun 19, 2014·Chemistry : a European Journal·Kazunobu IgawaKatsuhiko Tomooka

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