Investigating the mechanism of 1,3,5-cycloheptatriene formation: Condensation of 1-methylethyl 3-oxo-4-(triphenylarsoranylidene)butanoate with 7-methoxy-3,7-dimethyloctanal
Abstract:Condensation of [3‐(1‐methylethoxycarbonyl)‐2‐oxopropyl]triphenylarsonium bromide 8 with 7‐methoxy‐3,7‐dimethyloctanal 10 in the presence of a base gave bis(1‐methylethyl) 4,7‐dihydroxy‐2‐(6‐methoxy‐2,6‐dimethylheptyl)‐3,5,7‐cycloheptatriene‐1,3‐dicarboxylate 7b. The formation of 7b can be explained by a number of consecutive steps. The mechanism, strongly supported by liquid secondary ion mass spectrometry, suggests that an aldol condensation of the γ‐arsonium ylide 2b and the aldehyde 10 takes place as the i… Show more
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