Unsaturated macrocyclic compounds. LIX. Synthesis of four dehydro [16] annulenes and [16] annulene

IC Calder, Y Gaoni, F Sondheimer

Index: Calder,I.C. et al. Journal of the American Chemical Society, 1968 , vol. 90, p. 4946 - 4954

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Citation Number: 16

Abstract

Abstract: Oxidation of rrans-4-octene-l, 7-diyne (1) with oxygen, cuprous chloride, and ammonium chloride led to the cyclic dimer 2, the linear dimer 3, the linear trimer 4, the linear tetramer 5, and a chloro compound of unknown constitution. Treatment of the cyclic dimer 2 with potassium t-butoxide gave mainly phenylsuccindene-I0 (6), as well as smaller amounts of three dehydro [l6lannulenes (compounds A, B, and C). The data given in the present ...