Studies on Acetylenic Compounds. LV. Reactions of Phenyl 2-Propynyl Sulfone and Phenyl 3-Phenyl-2-propynyl Sulfone with Substituted Benzaldehydes

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Phenyl 2-propynyl sulfone (IV) and five kinds of benzaldehyde derivatives were treated with sodium hydride to give the corresponding 1 : 1 addition products, respectively. The structures were assigned to 1-phenylsulfonyl-4-substitutedphenyl-trans-3-buten-2-ones (V) based on the spectroscopic data. The confirmation of the elucidated structure was made by an alternative unambiguous synthesis which consisted of treating methyl phenyl sulfone and ethyl cinnamate with sodium hydride, affording V and 1-phenylsulfonyl-4-phenyl-3-penten-2-one (VI). When phenyl 3-phenyl-2-propynyl sulfone (VII) was treated with the five substituted benzaldehydes, were obtained similar products to V, 1 : 1 addition compounds of VII and benzaldehydes. These were assigned to be 1-phenylsulfonyl-3-phenyl-4-substitutedphenyl-3-buten-2-ones (VIII) by the spectroscopic data and the comparison with V. The plausible mechanism of the reaction and the physical properties of these products are presented in some detail.

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