The SRN1 mechanism in heteroaromatic nucleophilic substitution. Reactions involving certain dihalogenated. pi.-deficient nitrogen heterocycles

DR Carver, TD Greenwood, JS Hubbard…

Index: Carver, David R.; Greenwood, Thomas D.; Hubbard, James S.; Komin, Andrew P.; Sachdeva, Yesh P.; Wolfe, James F. Journal of Organic Chemistry, 1983 , vol. 48, # 8 p. 1180 - 1185

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Citation Number: 30

Abstract

Results With Dihalopyridines. Reactions involving 2, 3-and 3, 5-dichloropyridines (lc, d) and 2, 5-dibromopyridine (le) are summarized in Table I. Disubstitution products 3b-d were obtained after 15 min of photostimulation in the presence of excess 2 (expts 1, 3, and 5). In a series of experiments not detailed in Table I, lc-e were allowed to react with 2 under illumination for 1-5 min. In each instance only the original substrate and the appropriate ...