99054-11-2Relevant academic research and scientific papers
Application of the Intramolecular Aza-Wittig Reaction to the Synthesis of Vinylogous Urethanes and Amides
Lambert, P. H.,Vaultier, M.,Carrie, R.
, p. 5352 - 5356 (2007/10/02)
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.
