Studies on Acetylenic Compounds. LVII. Reactions of 2-Propynyl Sulfones with Cyclic Ketones

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Abstract

2-Butynyl phenyl sulfone (VI) and cyclic ketones were treated with sodium hydride to give the corresponding 1: 1 addition products, respectively. The structures were assigned to 1-phenylsulfonyl-3-(1-cyclohexenyl) 2-butanone (VII) and 2-phenylsulfonylmethylene-3-methyloxetane-4-spiro-1'-cyclohexane (VIII) in the case of cyclohexanone and assigned to 1-phenylsulfonyL-3-(1-cyclopentenyL) 2-butanone (XIII) in the case of cyclopentanone, respectively. Acid treatment of VIII afforded three degradation products, VII, X and XI, which confirmed the novel structure of VIII. 2-Propynyl p-tolyl sulfone (XIV) and cyclohexanone with sodium hydride treatment gave also an oxetane compound, XV. A plausible mechanism of the reaction and the physical properties of the products were presented in some detail.

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