Thiosilanes as Thioketalization Reagents

Author: Nesbitt, Stephen Lee

Year: 1977

Degree: Master's thesis

Advisor: Evans, David A.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/CDYJ-S314

Abstract

Thiosilanes react efficiently with simple aldehydes and ketones when catalyzed with ZnI_2 to produce thioacetals and thioketals. Steroidal diketones were thioketalized with yields and selectivity superior to other methods when allowed to react with thiosilanes and ZnI_2.

The overall thioketalization process proceeds through silyl-hemithioketal intermediates which can be detected and isolated from the reaction mixtures. The isolated silylhemithioketals can be resubmitted to the thioketalization reaction conditions and be converted to thioketals.

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