Photostimulated reactions of 2-bromopyridine and 2-chloroquinoline with nitrile-stabilized carbanions and certain other nucleophiles

MP Moon, AP Komin, JF Wolfe…

Index: Moon, Marcus P.; Komin, Andrew P.; Wolfe, James F.; Morris, Gene F. Journal of Organic Chemistry, 1983 , vol. 48, # 14 p. 2392 - 2399

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Citation Number: 27

Abstract

Potassiophenylacetonitrile (2) reacts with 2-bromopyridme (1) and 2-chloroquinoline (4) via the SRNl mechanism when the reactants are exposed to near-UV light in liquid NHa. Potassioacetonitrile (6) reacts similarly with 1 and 4 upon photostimulation; however, the phOto-SRN1 reaction with 1 is accompanied by SNAr2 amination which becomes the major reaction in the dark or in the presence of di-tee-butyl nitroxide. Substrate 4 undergoes ...