Five-and six-membered-ring formation from olefinic. alpha.,. beta.-epoxy ketones and hydrazine

G Stork, PG Williard

Index: Stork,G.; Williard,P.G. Journal of the American Chemical Society, 1977 , vol. 99, p. 7067 - 7068

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Citation Number: 29

Abstract

In the search for systems which might cyclize we finally discovered that epoxy ketone 4 was' cyclized with hydrazine in methanol to the hydrindenol5 in 85% yield. The structure of 5 (mixture of diastereoisomers) was strongly suggested by its NMR: 6 0.98 (2 d, J= 6 Hz, 3 H), 1.19 (2 s, 3 H), 1.21-2.90 (complex m, 10 H). In particular, the absence of vinyl hydrogen absorptions showed that essentially none of the" normal" Wharton product was formed. ...