Photochemical reactions of chromium-alkoxycarbene complexes with stabilized ylides to produce "push-pull" captodative allenes

Article abstract of DOI:10.1021/ja00037a008

Photolysis of chromium alkoxycarbene complexes in the presence of stabilized ylides produced allenes having electron withdrawing groups on C-1 and electron donating groups on C-3. These highly reactive captodative allenes rearranged to 1,3-substituted-1,3-dienes under mildly acidic conditions and hydrolyzed to γ-keto-α,β-unsaturated esters, both in excellent yield.