Tetrahedron letters

A convenient synthesis of dibenzo [a, c] cyclooctene based on thioenol ether reduction

PA Lottaz, TRG Edwards, YG Mentha, U Burger

Index: Lottaz, Pierre Andre; Edwards, Timothy R. G.; Mentha, Yves G.; Burger, Ulrich Tetrahedron Letters, 1992 , vol. 34, # 4 p. 639 - 642

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Citation Number: 4

Abstract

Abstract 9, 10, 11, 12-Tetrahydrodibenzo [a, b] cyclooctane-9, 12-diol (6) is found to be reluctant to double bond forming elimination. It gives a bridge ether (7) instead. The corresponding diketone (5) reacts with benzyl mercaptan to provide the bis-thioenol ether (8- a. The latter, upon treatment with Raney nickle, gives the desired title diene 1. An alternative approach to 1, based on repeated carbane addition to phenanthrene, is also presented.