Nucleophilic substitution reactions of (alkoxymethylene) dimethylammonium chloride

AGM Barrett, DC Braddock, RA James…

Index: Barrett, Anthony G. M.; Braddock, D. Christopher; James, Rachel A.; Koike, Nobuyuki; Procopiou, Panayiotis A. Journal of Organic Chemistry, 1998 , vol. 63, # 18 p. 6273 - 6280

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Citation Number: 49

Abstract

The use of imidate esters as potential replacements for diethyl azodicarboxylate and triphenylphosphine in the Mitsunobu reaction is described. A series of secondary alcohols were allowed to react with (chloromethylene) dimethylammonium chloride, generated from dimethylformamide (DMF) and oxalyl chloride, to give imidate esters. Reaction of these salts with potassium benzoate or potassium phthalimide gave the products of SN2 substitution ...

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