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 rearrangement products may themselves be further oxidised. In the presence of triethylsilane the carbocations are reduced prior to rearrangement
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