Abstract
Reaction of tropothione (1) with diphenylketene (2) gives regiospecifically an [8 + 2] cycloadduct (3) in high yield. Twisted phenyl groups in 2 intermix two vacant FMOs of the ketene moiety. This mixing brings about an appropriate site for the antisymmetric orbital interaction against the HOMO of 1. A phenyl carbon is found to assist this interaction.
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