Kinetic evidence for a novel, Grob-like substitution/fragmentation mechanism for the reaction of nucleophiles with trialkylammoniomethyl halides

…, WR Dolbier, L Zhang, Q Vu, WR Dolbier Jr

Index: Fletcher, Michelle O.; Zhang, Li; Vu, Quyen; Dolbier Jr., William R. Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 6 p. 1187 - 1192

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Abstract

Kinetic evidence is presented in favor of a concerted, bimolecular mechanism for the unusual nucleophilic substitution/fragmentation reactions of iodide ion with (halomethyl) trimethylammonium salts. The relative reactivities of allyl, ethyl and methyl groups for this Grob-like reaction are also determined. Activati