Photochemical Reactions of Chromium-Alkoxycarbene Complexes with Stabilized Ylides To Produce “Push-Pull” Captodative Allenes

Abstract

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 alienes 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. © 1992, American Chemical Society. All rights reserved.