The gas phase 1, 2-Wittig rearrangement is an anion reaction. A joint experimental and theoretical study

…, MS Taylor, JH Bowie, PCH Eichinger

Index: Sheldon, John C.; Taylor, Mark S.; Bowie, John H.; Dua, Suresh; Chia, C.S. Brian; Eichinger, Peter C. H. Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 2 p. 333 - 340

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Abstract

The migratory aptitudes of alkyl groups in the gas phase 1, 2-Wittig rearrangement have been determined experimentally as follows. An anion Ph––C (OR1)(OR2), on collisional activation, competitively rearranges to the two 1, 2-Wittig ions PhC (R1)(OR2)(O–) and PhC (R2)(OR1)(O–)[R1 and R2= alkyl and R1< R2]. These two ions respectively eliminate R2OH and R1OH. The smaller alkanol is eliminated preferentially, indicating that R2 (the larger ...