Dimethyl(alkyl) sulfates as Lewis acid type catalysts for acetalization and related reactions of carbonyl compounds.

ABSTRACT: The catalytic activity of dimethyl sulfate (DMS) and its higher homologs in converting carbonyl compounds to O,O-dimethylacetal/ketals is demonstrated. Our mechanistic investigations proved that previously reported Schmitz and Langvad claims stating DMS as an alkylating agent and a source of sulfuric acid in the acetalization of aldehydes were erroneous. Carbonyl compounds were converted to methyl, ethyl acetals/ketals, 1,3-dioxalanes and 1,3-dioxanes, and cyclohexane-1,3-diones into vinylogous esters. Selective aldehyde protection and ketone reduction were preferentially achieved in a single step. This study represents the first instance of using alkylating agents, such as dimethyl, diethyl, diisopropyl, and di-n-butyl sulfates, as catalysts in organic transformations

SUBMITTER: Sarkar T 

PROVIDER: S-EPMC12452085 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature