Generation and oligomerization of bicyclo [2.2. 2] octyne and properties of tris (bicyclo [2.2. 2] octeno) benzene obtained from the linear trimer

…, S Aonuma, Y Jinbu, R Tsuji, C Hirosawa…

Index: Komatsu, Koichi; Aonuma, Shuji; Jinbu, Yasuhisa; Tsuji, Ryotaro; Hirosawa, Chitaru; Takeuchi, Ken'ichi Journal of Organic Chemistry, 1991 , vol. 56, # 1 p. 195 - 203

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Citation Number: 60

Abstract

Reaction of 2, 3-dibromobicyclo [2.2. 2] oct-2-ene (10) with n-butyllithium in THF at-78" C affords a series of oligomeric dibromides 11 (n= 2-5), which are composed of linearly bonded bicyclo [2.2. 2] oct-2-ene units. A trapping experiment indicated that the reaction proceeds via formation of a highly strained acetylene, bicyclo [2.2. 2loctyne (18), as a reactive intermediate. Upon treatment with sodium naphthalenide, the trimer 11 (n= 3) ...