Heterocycles from Phosphonium−Iodonium Ylides. Photochemical Synthesis of λ5-Phosphinolines
The Journal of Organic Chemistry2009Vol. 74(24), pp. 9428–9432
Citations Over TimeTop 20% of 2009 papers
E. D. Matveeva, Tatyana A. Podrugina, Anna S. Pavlova, А. В. Миронов, Anatoliy A. Borisenko, Rolf Gleiter, Н. С. Зефиров
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.
Related Papers
- → Stable Phosphonium Sila-ylide with Reactivity as a Sila-Wittig Reagent(2009)69 cited
- → NHC Core Phosphonium Ylide-based Palladium(II) Pincer Complexes: The Second Ylide Extremity Makes the Difference(2020)30 cited
- → Comparison of basicity of some arsonium and phosphonium ylides(1968)18 cited
- → The Mechanism and Stereochemistry of Wittig Reactions of Phosphonium Ylide-Anions(1990)8 cited
- → Synthesis and reactivity of [M(η3-allyl)(η2-amidinato)(CO)2(phosphonium ylide)] (M = Mo, W): Investigation of the ligand properties of phosphonium ylides(2017)2 cited