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

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 we...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-12, Vol.74 (24), p.9428-9432
Main Authors: Matveeva, Elena D, Podrugina, Tatyana A, Pavlova, Anna S, Mironov, Andrey V, Borisenko, Anatoliy A, Gleiter, Rolf, Zefirov, Nikolay S
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:1520-6904
DOI:10.1021/jo901984q