gem-Dihalides from α-Haloamides. III. Rearrangement of Optically Active α-Chlorohydrocinnamamides

CL Stevens, H Dittmer, J Kovacs

Index: Stevens,C.L. et al. Journal of the American Chemical Society, 1963 , vol. 85, p. 3394 - 3396

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Citation Number: 3

Abstract

Additional evidence for the stereospecific nature of the conversion of a-haloamides to gem- dihalides was gained by the isolation of an opticall!-active geni-dihalide from an opticallp active a-haloamide. Da-Chloroliydrocinnamarnide,[a] 2 5~+ 1 l. Oo, was dissolved in alkaline sodium hypobromite and steam distilled to yield~-gem-diIialide, a Z 5~-0.065', deterrnirietl as a neat liquid with DL-gem-dihalide as reference. Similarly,~-a-chloroh~ drr) ...