Reaction of allyl iminophosphoranes with ketenes and acyl chlorides: One-pot preparation of 4-pentenenitriles

Article abstract of DOI:10.1016/S0040-4020(01)81880-9

One-pot conversion of allylazides into 4-pentenenitriles 4 is achieved by sequential treatment of allyl azides with triphenylphosphine and the corresponding ketene under mild and neutral conditions. On the other hand, allyl iminophosphoranes and related react with arylacetic acid chlorides to give unexpectedly the phosphonium salts 5 which by treatment with base and then heating lead to 4-pentenenitriles 9.