Journal of the American Chemical Society

Base-induced rearrangement of. gamma.-diketones. II. Demonstration of the occurrence of skeletal rearrangement and of the reversibility of the reactiion

P Yates, MJ Betts

Index: Yates,P.; Betts,M.J. Journal of the American Chemical Society, 1972 , vol. 94, p. 1965 - 1970

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Citation Number: 5

Abstract

2-3C with diphenylketene to give 4-hydroxy-2, 2, 4-tripheny1-3-butenoi~-3-~~ C acid lactone followed by treatment of the lactone with tert-butyllithium, gave 5, 5-dimethyl-1, 2, 2-triphenyl- l, 4-hexanedione-3-3C on treatment in ether with sodium methoxide. The occurrence of skeletal rearrangement is thus demonstrated, and it is concluded that the base-induced interconversion of y-diketones involves the intermediacy of homoenolate ions rather than ...