Journal of Organic Chemistry p. 5352 - 5356 (1985)
Update date:2022-08-05
Topics:
Lambert, P. H.
Vaultier, M.
Carrie, R.
The treatment of ω-azido β-dicarbonyl derivatives with 1 equiv of triphenylphosphine leads to a transient phosphinimine (Staudinger reaction), which cyclizes into vinylogous urethanes and amides via an intramolecular aza-Wittig reaction in excellent yields.The starting azides were obtained by a nucleophilic substitution by NaN3 in Me2SO on the corresponding ω-halo β-dicarbonyl derivatives that were accessible by the γ-alkylation of β-dicarbonyl compounds with α,ω-dihaloalkanes.
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(1985)