α,α-Diacetyl Cyclic Ketene Dithioacetals: Odorless and Efficient Dithiol Equivalents in Thioacetalization Reactions

Abstract

Two novel, non-thiolic, odorless dithiol equivalents, α,α-diacetyl cyclic ketene dithioacetals 2a and 2b, had been developed. A range of carbonyl compounds 3 were converted into corresponding dithioacetals, dithianes 4 and dithiolanes 5, in high yields (up to 99%) in the presence of 2a or 2b. Moreover, 2a and 2b show high chemoselectivity between aldehyde and ketone in thioacetalization.

Key words

aldehyde - α,α-diacetyl cyclic ketene dithioacetal - thiol - thioacetalization - ketone

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10

All dithioacetals 4, 5 and 9 prepared in the present work are known compounds and were identified by ¹H NMR, IR spectroscopy and elemental analyses, the data for these compounds are in good agreement with that in literatures.