Unsaturated Macrocyclic Compounds. XXV. 1 The Synthesis of Bisdehydro-[20]-annulene,[20] Annulene, Tridehydro-[30] annulene and [30] Annulene from 1, 5, 9- …

F Sondheimer, Y Gaoni

Index: Sondheimer,F.; Gaoni,Y. Journal of the American Chemical Society, 1962 , vol. 84, p. 3520 - 3526

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Citation Number: 19

Abstract

Two syntheses of 1, 5, 9-decatriyne (V) are described. The osidative coupling of this triacetylene with cupric acetate in pyridine yielded the cyclic dimer IX and cyclic trimer XII, as well as the linear dimer VIIIa and linear tetramer VIIIb. The cyclic dimer IX was rearranged with potassium t-butoxide in t-butyl alcohol to bisdehydro-[20] annulene (eg, X), which was converted by partial hydrogenation to j201annulene (eg, XI). Similarly, the cyclic trimer XI1 ...