The Journal of Organic Chemistry

A multistep rearrangement from 2, 2-disubstituted-1, 3-cyclohexanediones to 3-substituted 2-cyclohexenones via phosphonate anions and its application to a formal …

Y Yamamoto, T Furuta

Index: Yamamoto, Yoshinori; Furuta, Toshiaki Journal of Organic Chemistry, 1990 , vol. 55, # 13 p. 3971 - 3972

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Citation Number: 15

Abstract

Summary: The reaction of 2, 2-disubstituted 1, 3-cyclohexanediones (1) with dimethyl methylphosphonate anion in the presence of trimethylsilyl chloride produces 3-substituted 2- cyclohexenones (2) in moderate to very good yields. This new overall reaction is accounted for by (a) attack of the phosphonate anion on a carbonyl group,(b) retro-aldol cleavage,(c) reorganization of the acidic proton, and (d) an intramolecular Wadsworth-Emmonds ...