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Abstract
Quinone methide (1) reacts with excess carbmethoxymethylenetriphenylphosphorane (2a) to afford the new product 3a–6 whereas, with carbethoxymethylenetriphenylphosphorane (2b) yielded 3b, 4b, 13 and 14. It was also found that the polarity of the solvent has a limited role in the course of the reaction and in the yield of the condensation products of 1 and ylides 2. Mechanistic studies suggest that 10-methyleneanthrone (1) can react as a Diels-Alder diene and function as a dienophile in the same reaction. When the Wittig reaction was carried out on the new ylides 5 and 6 using benzaldehyde, the new olefins 16 and 17 were isolated.