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Cycloadducts of 1‐Alkyl‐1,2‐diphospholes with N‐Phenylmaleimide: Synthesis, Structure, Oxidation, and Thionation Reactions

Cycloadducts of 1‐Alkyl‐1,2‐diphospholes with N‐Phenylmaleimide: Synthesis, Structure, Oxidation,... The [4+2] cycloaddition reaction of 1‐alkyl‐1,2‐diphospholes (1) with N‐phenylmaleimide proceeds at 25°С in toluene to give 1,7‐diphosphanorbornenes (2) as anti‐endo isomer only. Oxidation of 2 with air at room temperature or thionation with excess of sulfur at 80°С results in the formation of mixed valent PIII, PV 7‐oxo(thia)‐1,7‐diphosphanorbornenes (3, 4) in high yield. The polycyclic compounds 3 and 4 are air stable and have small sums of valence angles at the phosphorus atoms. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Cycloadducts of 1‐Alkyl‐1,2‐diphospholes with N‐Phenylmaleimide: Synthesis, Structure, Oxidation, and Thionation Reactions

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References (16)

Publisher
Wiley
Copyright
"Copyright © 2014 Wiley Periodicals, Inc."
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.21132
Publisher site
See Article on Publisher Site

Abstract

The [4+2] cycloaddition reaction of 1‐alkyl‐1,2‐diphospholes (1) with N‐phenylmaleimide proceeds at 25°С in toluene to give 1,7‐diphosphanorbornenes (2) as anti‐endo isomer only. Oxidation of 2 with air at room temperature or thionation with excess of sulfur at 80°С results in the formation of mixed valent PIII, PV 7‐oxo(thia)‐1,7‐diphosphanorbornenes (3, 4) in high yield. The polycyclic compounds 3 and 4 are air stable and have small sums of valence angles at the phosphorus atoms.

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 2014

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