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2005
Intermediates
O 0190
Generation and Reaction of Ammonium Ylides in Basic Two-Phase Systems —
reaction of ammonium ylides, generated from quaternary ammonium salts (I) un27- 046 The
der alkaline conditions with various electrophilic agents is studied. Thus, reaction with
alkenes (II) and (V) provides access towards cyclopropane derivatives (III)/(IV) and
(VI), resp., in good yields, the cis—trans selectivity being determined by the substrate
structure. Reaction with alkyl halides (VII) gives cyanoalkenes (VIII). When allylation
agents like (VIIa) are used, the cyclopropanation of the γ,δ-double bond [cf. (IX)] is
possible by change of the substrate ratio. The reaction of ammonium ylides with aldehydes (XI) gives cyanooxiranes with good to excellent cis-selectivity. —
(KOWALKOWSKA, A.; SUCHOLBIAK, D.; JONCZYK*, A.; Eur. J. Org. Chem.
2005, 5, 925-933; Fac. Chem., Warsaw Univ. Technol., PL-00-662 Warszawa, Pol.;
Eng.) — Mischke
2005
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