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■ Silver Ion-mediated Desulfurization-Condensation of Thiocarbonyl Compounds

Isao Shibuya,* Yasuo Gama, Masao Shimizu, and Midori Goto

*National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan

Abstract

The title reaction of N-hydroxybenzamide with aryl isothiocyanates at ambient temperature gave 5-(arylimino)-3-phenyl-1,4,2-dioxazoles (1, 2) with elimination of Ag₂S. The structure of 1 was determined by X-Ray crystal structure analysis. N-Hydroxybenzamide also reacted with diaryl thioketones to afford condensation products, 5,5-diaryl-3-phenyl-1,4,2-dioxazoles(3, 4). Desulfurizations of diaryl thioketones with α-hydroxy acids and with salicylic acid gave in the same way 2,2-diaryl-5-phenyl-1,3-dioxolan-4-ones (5-8) and 2,2-diaryl-1,3-benzodioxan-4-ones (9-11), respectively. N-Phenylglycine and N-methylanthranilic acid gave similar types of condensation products (12, 13).