Efficient guaiazulene and chamazulene syntheses involving [6+ 4] cycloadditions

D Mukherjee, LC Dunn, KN Houk

Index: Mukherjee,D. et al. Journal of the American Chemical Society, 1979 , vol. 101, # 1 p. 251 - 252

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Citation Number: 32

Abstract

(4) Addition of> 1 equiv of LDA to the tosylhydrazone will cause some fragmentation to a nitrile (see ref 1): RCH= NNHTs-RCN. If the resulting nitrile has acidic CY protons, the derived anion will form and will attack starting tosylhydrazone to afford alkene products of" self-condensation". This side reaction is seen in trace amounts with most reactions in Tables I and II.(5) RH Shapiro, Org. React., 23, 405 (1976).(6) Shapiro elimination is not normally ...