Our group has reported several examples of [4+4] photocycloaddition between 1,3-enyne and 2-pyridone �  a new type of cycloaddition for the conjugated enynes.1 The major complication in this reaction is instability of the primary 1,2,4-cyclooctatriene adducts  which tend to undergo further [2+2] dimerizations. Current work describes our efforts to overcome this problem by introducing steric hindrance to stabilize this cyclic allene intermediate and the first examples of intramolecular allene trapping, for instance via [3+2] cyclization with azides.

Recent developments in enyne-pyridone [4+4] photocycloadditions

244th National Meeting (2012)

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