The Journal of Organic Chemistry

Synthesis and cycloaddition reactions of acetylenic iminium compounds

JS Baum, HG Viehe

Index: Baum,J.S.; Viehe,H.G. Journal of Organic Chemistry, 1976 , vol. 41, p. 183 - 187

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Citation Number: 59

Abstract

Phenyl, tert-butyl, and unsubstituted propiolamidium tetrafluoroborate salts, prepared from ready alkylation of acetylenic amides with triethyloxonium fluoroborate, undergo facile Diels- Alder cycloaddition with cyclopentadiene. Propiolamidium salts also react easily with tetraphenylcyclopentdienone, ethyl diazoacetate, and a mesoionic oxazolium compound. A qualitative comparison of the activation of multiple bonds toward cycloaddition by the ...