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Synlett 2004(6): 999-1002
DOI: 10.1055/s-2004-822892
DOI: 10.1055/s-2004-822892
LETTER
© Georg Thieme Verlag Stuttgart · New York
α,α-Diacetyl Cyclic Ketene Dithioacetals: Odorless and Efficient Dithiol Equivalents in Thioacetalization Reactions
Further Information
Received
24 February 2004
Publication Date:
25 March 2004 (online)
Publication History
Publication Date:
25 March 2004 (online)
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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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References
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.