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

Kazunobu Igawa, Yuuya Kawasaki, Sora Nozaki, Naoto Kokan, Katsuhiko Tomooka

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)4165-4171
Number of pages7
JournalJournal of Organic Chemistry
Volume85
Issue number6
DOIs
Publication statusPublished - Mar 20 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Ozone Oxidation of Silylalkene: Mechanistic Study and Application for the Synthesis of Silacarboxylic Acid Derivatives'. Together they form a unique fingerprint.

Cite this