Heterocycles from phosphonium-iodonium ylides. Photochemical synthesis of lambda(5)-phosphinolines

J Org Chem. 2009 Dec 18;74(24):9428-32. doi: 10.1021/jo901984q.

Abstract

A photochemical reaction of mixed phosphonium-iodonium ylides with acetylenes yielding lambda(5)-phosphinolines, a rare class of phosphorus heterocycles hardly accessible by other methods, was found. The yields of lambda(5)-phosphinolines vary from 35% to 80%. The structures of two phosphinolines were established by single-crystal X-ray diffraction. The X-ray diffraction and NMR spectra data indicate the superposition of ylidic and aromatic structures for phosphinolines.