119842-40-9Relevant articles and documents
Direct Conversion of Nitriles into Alkene “Isonitriles”
Li, Yajun,Fleming, Fraser F.
supporting information, p. 14770 - 14773 (2016/11/23)
The sequenced addition of RLi to nitriles, trapping with isopropylformate, and dehydration with phosphoryl chloride provides an efficient, direct synthesis of alkene isocyanides. The one-pot sequence involves a series of carefully orchestrated steps: addition, formylation, tautomerization, and dehydration, with CuCN catalyzing a key equilibration of a formyl imine to an N-formyl enamine. The resulting aromatic alkeneisocyanides, that are otherwise challenging to synthesize, engage in an unusual [4+2]-type cycloaddition/1,3-H shift/decyanation sequence to afford substituted naphthalenes.
REDUCTIVE FORMYLATION OF OXIMES; AN APPROACH TO THE SYNTHESIS OF VINIL ISONITRILES
Barton, H. R. Derek,Bowles, Timothy,Husinec, Suren,Forbes, Judith E.,Llobera, Antonia,et al.
, p. 3343 - 3346 (2007/10/02)
Reduction of ketoximes using anhydrous titanium-(III)-acetate in the presence of mixed formic-acetic anhydride yields N-formyl enamines whichmay be dehydrate to vinyl isonitriles