Abstract
Photoreactions of several arylalkylcyclopropenethiones (1b-e) have been investigated. The products formed have been rationalized on the basis of \alpha-cleavage as the primary photoprocess. The photochemical \alpha-cleavage is presumed to originate from the lowest excited $n\pi^*$ riplet state. A ioselective \alpha-cleavage reaction has been observed and this unusual regioselectivity is explained on the basis of close approach of the ground-state energy surface of the diradical/carbene, the primary intermediates, to the excited triplet-state surface of cyclopropenethiones. Reactions originating from both triplet and singlet thioketene carbene have been observed upon photolysis of arylalkylcyclopropenethiones.
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