Steroidal 5-keto-4,5-seco-3-ynes of the estrane, androstane, and pregnane series are prepared from 3-keto-4-dehydro steroids via the 3-hydrocarbon-sulfonylhydrazono-4,5-oxido derivative thereof which undergoes fission and rearrangement in situ to form the 5-keto-4,5-seco-3-yne structure. The 6- and/or 10-hydrocarbon substituted-5-keto-4,5-seco-3-ynes are prepared by reacting a 6- and/or 10-unsubstituted-5-keto-4,5-seco-3-yne in an alkylating medium with a hydrocarbon sulfonate or, preferably, a hydrocarbon halide.
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