Tetrahedron

The synthesis of octavalene (tricyclo [5.1. 0.0 2, 8] octa-3, 5-diene) and several substituted octavalenes

M Christl, R Lang, C Herzog

Index: Christl, Manfred; Lang, Reinhard; Herzog, Clemens Tetrahedron, 1986 , vol. 42, # 6 p. 1585 - 1596

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Citation Number: 14

Abstract

The first synthesis of octavalene (1a) is reported. The starting material is homobenzvalene (5), to which monobromocarbene is added. The resulting compound 3a takes up bromine across the central bicyclo [1.1. 0] butane bond to form the tribromide 7a which undergoes a cyclopropyl bromide-allyl bromide rearrangement on heating. From the product (1Oa) HBr is eliminated to give a 1, 3-dibromocyclobutane with a 1, 3-butadiene bridge across its 2-and ...