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Communication | Special issue | Vol 18, No. 1, 1982, pp.83-86
Published online, 1st January, 1970
DOI: 10.3987/S(B)-1982-01-0083
Chemistry of 2,2-Dimethyl-1,3-dioxole. Two-carbon Homologation of Carbonyl Compounds to α-Ketoaldehydes and Dihydroxyacetonyl Moieties

Daniel L. Flynn, Lester A. Mitscher,* Tarik Veysoglu, and Zbigniew Wielogorski

*Department of Medicinal Chemistry, Kansas University, Lawrence, Kansas 66045, U.S.A.

Abstract

The lithium salt of 2,2-dimethyl-1,3-dioxole adds readily to aldehydes and ketones to form the blocked dihydroxyacetonyl moiety. Only in favorable cases, however, can deblocking be accomplished without rearrangement. More commonly, acid-catalyzed deblocking leads to concommitant dehydration and results in excellent yields of α-ketoaldehydes rather than substituted dihydroxyacetones.