Barrelene, a New Convenient Synthesis

S Cossu, S Battaggia, O De Lucchi

Index: Cossu, Sergio; Battaggia, Simone; Lucchi, Ottorino De Journal of Organic Chemistry, 1997 , vol. 62, # 12 p. 4162 - 4163

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Citation Number: 18

Abstract

Barrelene (bicyclo [2.2. 2] octa-2, 5, 7-triene, 1) is the formal Diels-Alder adduct of acetylene to benzene. 1 Since neither acetylene nor benzene is reactive in cycloaddition reactions, the synthesis of 1 requires the definition of both an efficient acetylene equivalent2 and of a reagent able to temporarily suppress the aromatic character of benzene, in such a way as to allow it to react as a diene. 3 In other words, this equals the definition of a synthon of ...

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