Journal of the Chemical Society. Perkin transactions II p. 1763 - 1768 (1990)
Update date:2022-08-17
Topics:
Eichinger, Peter C.H.
Bowie, John H.
Deprotonation of alkyl vinyl ethers (CH2=CHOR) with NH2- in the gas phase yields the two carbanions CH2=C(-)OR and C(-)H=CHOR.The former ion can be synthesized specifically using the SN2(Si) reaction CH2=C(SiMe3)OR + NH2- --> CH2=C(-)OR + Me3SiNH2: the ion undergoes several competitive and characteristic collision-induced reactions.For example, (i) when R >/= Et, elimination of an alkene, i.e.CH2=C(-)OR --> (CH2CHO)- + R-H, and (ii) the Wittig rearrangement CH2=C(-)OR --> CH2=C(R)O-.
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