Crystalline-State Photoisomerization of α,β-Unsaturated Thioamide Analyzed by X-rays

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  • Crystalline State Photoisomerization of アルファ ベータ Unsaturated Thioamide Analyzed by X rays

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<jats:title>Abstract</jats:title> <jats:p>When a crystal of N,N-dibenzyl-1-cyclohexenecarbothioamide was exposed to UV light at 263 K, the cell dimensions were gradually changed with retention of the single crystal form. Since the crystal gradually decomposed after 330 h, the irradiation was stopped and the structure was analyzed by X-rays. The thioamide molecule was converted by 65.0% to the thiolactam molecule. The thioamide and thiolactam molecules were observed as a disordered structure in the crystal. The disordered structure clearly indicates that the hydrogen atom of one of the benzyl groups is extracted by one of the olefin carbon atoms of the cyclohexenyl group and that the benzyl carbon atom makes a bond with another olefin carbon to form a thiolactam ring. The mechanism of the ring formation and the chirality of the produced thiolactam are well explained from the reaction cavity.</jats:p>

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