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Communication | Special issue | Vol 37, No. 1, 1994, pp.137-147
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S6
Reaction of 2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octane Lignans

Andrew Pelter* and Robert S. Ward

*Chemistry Department, University of Swansea, Singleton park, Swansea SA2 8PP, U.K.

Abstract

Reactions of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans (furofurans) have been rationalised in terms of the production of stabilised carbocations. These may be produced by acid catalysed or oxidative reactions dependant on the constitution of the lignan substrate. The carbocations may then undergo rearrangements in the case of acid catalysed reactions or the reanangement products may themselves be funher oxidised. In the presence of hiethylsiie the carbocations are reduced prior to rearrangement.