PET reactions of cis-dibenzoylalkenes: an efficient trans-reduction of C=C bond.

In contrast to its reaction under catalytic hydrogenation, the first instance of an exclusive and chemoselective trans-reduction of the ene part of derivatives of 5,6-dibenzoylbicyclo[2.2.2]oct-5-en-2-one has been reported under moderate photoinduced electron transfer (PET) conditions using triethylamine (TEA). In the absence of TEA, such molecules underwent 1,5-photophenyl migration yielding vinyl ketenes.