Deprotection of Acetals and Silyl Ethers Using Some <i>π</i>-Acceptors

Abstract

Abstract Hydrolysis of dodecanal dimethyl acetal and dodecyl silyl ethers in MeCN–H2O was examined using a catalytic amount of π-acceptors such as 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), tetracyanoethylene (TCNE), 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (TCNQF4), and chloranil (CA). Cleavage of dodecyl triethylsilyl ether with TCNQ and CA was caused by room light. By application of DDQ-catalyzed deprotection of acetals to hydrolysis of tetrahydropyranyl ethers, the corresponding alcohols were obtained in quantitative yields.