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

研究成果: ジャーナルへの寄稿学術誌査読

2 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)4165-4171
ページ数7
ジャーナルJournal of Organic Chemistry
85
6
DOI
出版ステータス出版済み - 3月 20 2020

!!!All Science Journal Classification (ASJC) codes

  • 有機化学

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