Cyclization Reaction of Bis(tributylstannylated) α-Ketols with Heterocumulenes. Preparation of O,O-Vinylene Imino- and Thiocarbonates

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Abstract
Aromatic α-ketols reacted with diethylaminotributylstannane at 60 °C to afford a mixture of (Z)- and (E)-1,2-bis(tributylstannyloxy)-1,2-diarylethenes, which were allowed to react with organic isothiocyanates and carbon disulfide to give substituted O,O-vinylene imino- and thiocarbonates, respectively. Aliphatic α-ketol, 3-hydroxy-2-butanone, was treated by the aminostannane, followed by the reaction with carbon disulfide to form (E)-1,2-bis(tributylstannylthio)-2-butene.