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1 Polish Journal of Chemistry

1 1999

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A novel type of ring closure of amino-substituted thiocarbonyl ylides

Romański J., Mlostoń G., Linden A., Heimgartner H.

Polish Journal of Chemistry

1999

vol. 73 nr 3

475-485

The reaction of 4,4-dimethyl-1,3-thiazole-5(4H)-thiones 7a-c with dimethyl 2-diazo-3-(phenyloamino)butanoate (2), prepared from dimethyl fumarate and phenyl azide, in toluene at 800C yielded mixtures of dimethyl 2-(4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-ylidene)-3-(N-phenylamino)butanedioates of type 11 and four diastereoisometric 4,4-dimethyl-9-phenyl-1,6-dithia-3,9-diazaspiro[4,4]non-2-ene-7,8-dicarboxylates of type 12. The formation of the products of type 12 is rationalized by a novel cyclization of intermediate thiocarbonyl ylides 9. The structures of cis-12a, cis-12c, and trans-12c were established by X-ray crystallography.