Cycloaddition. XVIII. Electrophilic addition of chlorosulfonyl isocyanate to ketones. Reaction with aromatic ketones

A Hassner, JK Rasmussen

Index: Hassner,A.; Rasmussen,J.K. Journal of the American Chemical Society, 1975 , vol. 97, p. 1451 - 1459

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Citation Number: 12

Abstract

Abstract: Electrophilic addition of chlorosulfonyl isocyanate (CSI) to “aromatic” ketones 1 (R'COCH2RZ, R1 and/or R2= aryl) was found to be a synthetically versatile reaction, producing 2H-1, 3-oxazine-2, 4 (3H)-diones (6) when dichloromethane was the solvent and 1, 2, 3-oxathiazin-4 (3H)-one 2, 2-dioxides (4) as well (if R'= aryl) in diethyl ether solvent. A number of additional products are observed in low yield. An examination of substituent ...

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