1, 2-, 1, 4-, 1, 5-, and 1, 6-Halogen participation in the trifluoroacetolysis of primary alkyl nosylates

PE Peterson, JF Coffey

Index: Peterson,P.E.; Coffey,J.F. Journal of the American Chemical Society, 1971 , vol. 93, p. 5208 - 5213

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Citation Number: 14

Abstract

Abstract: The trifluoroacetolyses of the following p-nitrobenzenesulfonates were studied: 2- chloro-l-propyl, 3-chloro-l-butyl, 4-chloro-l-pentyl, 5-chloro-1-hexyl, 6-chloro-1-heptyl, and 5- bromo-1-hexyl. Trifluoroacetolysis of 2-chloro-1-propyl and 4-chloro-1-pentyl nosylates gave substantially quantitative 1, 2-and 1, 4-halogen shifts. The extent of halogen shift was reduced to 90% for 5-chloro-1-hexyl nosylate and-17z for 6-chloro-1-heptyl nosylate. Rate ...