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

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

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被引用次数: 14

摘要

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 ...