Ylide vs. 1, 4-cycloaddition in the interaction of an alkylidenecarbene with azoarenes and the formation of 2H-indazoles and tetrahydrotetrazoles

K Krageloh, GH Anderson, PJ Stang

Index: Krageloh,K.; Anderson,G.H.; Stang,P.J. Journal of the American Chemical Society, 1984 , vol. 106, p. 6015

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Citation Number: 20

Abstract

Abstract: Reaction of substituted ambenzenes with isopropylidenecarbene (CH3) 2C= C:, generated from either 2-methyl-1-propenyl triflate and t-BuOK or silylvinyl triflate (CH3) 2C= C (OTf) SiMe3 and benzyltrimethylammonium fluoride (BTAF), gave 2H-indazoles in moderate yield. Indazoles were identified by spectral means as well as independent synthesis. A two-step mechanism, involving an ylide-type intermediate, is proposed for ...