Sulfuryl chloride gibberellin epoxides

Treatment of 1,1-disubstituted epoxides of the gibberellin family with sulfuryl chloride results in the formation of the corresponding a,3-enal in good yield, as shown in equation (31). Four examples were reported in which alcohols, esters, lactones and dkenes survive. The postulated mechanism involves an electrophilic opening of the epoxide with elimination, followed by oxidation of the primary chlorosulfate ester. A steroidal 3-spirooxirane also undergoes this reaction, but the yield is poor and several products are obtained, suggesting that the overall scope of this reaction may be limited. 

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