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
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.
Topics & Concepts
OzonideSilylationOzoneChemistryCleavage (geology)OzonolysisReaction mechanismPrimary (astronomy)Oxidative cleavageCombinatorial chemistryOrganic chemistryCatalysisMaterials sciencePhysicsFracture (geology)Composite materialAstronomyOxidative Organic Chemistry ReactionsOrganoboron and organosilicon chemistryChemical Synthesis and Reactions