Abstract
The coupling of vinylic ylide (3) synthesized from AsPh3 (2) and dimethyl acetylenedicarboxylate (DMAD) (1) with tropylium fluoroborate (4) in CH2Cl2 was found to give 3-phenyl-1,2-dicarbomethoxyprop-2-enylidentriphenyl arsonium salt (5) via ring contraction of cycloheptatriene. Treatment of the latter (5) with aqueous sodium hydroxide gives 3-phenyl-1,2-dicarbomethoxyprop-2-enylidentriphenylarsorane (6, Z-isomer), and this efficiently isomerized to E-isomer (7) under sunlight irradiation.
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