REACTION OF ALLYL IMINOPHOSPHORANES WITH KETENES AND ACYL CHLORIDES -ONE-POT PREPARATION OF 4-PENTENENITRILES

Authors
MOLINA P ALAJARIN M LOPEZLEONARDO C ALCANTARA J
Citation
P. Molina et al., REACTION OF ALLYL IMINOPHOSPHORANES WITH KETENES AND ACYL CHLORIDES -ONE-POT PREPARATION OF 4-PENTENENITRILES, Tetrahedron, 49(23), 1993, pp. 5153-5168
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
23
Year of publication
1993
Pages
5153 - 5168
Database
ISI
SICI code
0040-4020(1993)49:23<5153:ROAIWK>2.0.ZU;2-7
Abstract
One-pot conversion of allyl azides into 4-pentenenitriles 4 is achieve d by sequential treatment of allyl azides with triphenylphosphine and the corresponding ketene under mild and neutral conditions. On the oth er hand, allyl iminophosphoranes and related react with arylacetic aci d chlorides to give unexpectedly the phosphonium salts 5 which by trea tment with base and then heating lead to 4-pentenenitriles 9.