Unsaturated macrocyclic compounds. XVII. 1 The prototropic rearrangement of linear 1, 5-enynes to conjugated polyenes. The synthesis of a series of vinylogs of …

F Sondheimer, DA Ben-Efraim…

Index: Sondheimer,F. et al. Journal of the American Chemical Society, 1961 , vol. 83, p. 1675 - 1681

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Citation Number: 197

Abstract

It is shown that 1, 5-enynes are rearranged to conjugated polyenes by means of potassium t- butoxide in t-butyl alcohol. The method is used for the synthesis of a series of vinylogs of butadiene, containing 3, 5, 6, 8 and 10 conjugated double bonds. The ultraviolet spectra data of this simplest possible class of conjugated polyene are discussed briefly.