Syntheses and Cycloaddition Reactions of Thiaazulenocyclone and Thiaazulenocyclone 8,8-Dioxide

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Thiaazulenocyclone (2) and thiaazulenocyclone 8,8-dioxide (3) were synthesized and their reactions were investigated. The reaction of 2 with N-phenylmaleimide and the reactions of 2 or 3 with acenaphthylene and norbornene provided the Diels-Alder endo adducts, but cycloaddition reactions of 2 or 3 with acetylenic dienophiles, maleic anhydride or benzyne yielded decarbonylated products derived from the [4+2] adducts. The adduct of 2 and N-phenylmaleimide was a mixture of two stereoisomers and was decarbonylated on heating. The reactivities of 2 and 3 in the cycloaddition reactions were estimated by consideration of the frontier orbital interaction. The stereospecificity was mainly controlled by the steric and dipole-dipole interactions.
公益社団法人日本薬学会の論文
1981-05-23