The Journal of Organic Chemistry

Synthesis of exo-bicyclo [2.2. 2] oct-5-ene-2, 3-dicarboxylic anhydrides by thermal isomerization of trans-diacids

A Weisz, A Mandelbaum

Index: Weisz, Adrian; Mandelbaum, Asher Journal of Organic Chemistry, 1988 , vol. 53, # 25 p. 5812 - 5815

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Citation Number: 7

Abstract

Clearly species 2 is the least ”homoaromatic” or “anthracene-like” and the most “annulene-like”. The fact that carbon 7 is the thermodynamically favored protonation site in 3 but not in 2 follows the same pattern and agrees with simple frontier MO theory considerations. Most likely, in 2 the increased strain in the central ring caused by protonation at positions 7 or 14 is not com- pensated by transannular stabilization as it is in the case ...