RATIONAL TEST FOR POSSIBLE ZINCACYCLOBUTANE ION IN THE GUSTAVSON REACTION

Article abstract of DOI:10.1016/S0022-328X(00)85522-9

The possibility of obtaining a zincacyclobutane intermediate in the Gustavson reaction was hypothesized to explain the formation of olefins obtained in this reaction.A select group of substrates was investigated in which the formation of olefin products could be explained if one invoked the intermediacy of a zincacyclobutane, but would be difficult to explain in the absence of such an intermediate.A deuterium-labeled substrate was also investigated and the olefins obtained from its reaction with zinc were found to closely follow the deuterium-labeling pattern obtainedfrom the decomposition of the analogous deuterium-labeled platinacyclobutane.