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Reactivity of phosphiranes toward nucleophiles: Theoretical and experimental investigations

✍ Scribed by Michelle L. Coote; Elizabeth H. Krenske; Ilham Maulana; Jörg Steinbach; S. Bruce Wild

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
151 KB
Volume
19
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The thermodynamic and kinetic parameters for the reaction of 1‐methylphosphirane with dimethylphosphide (PMe), proceeding via attack at the ring phosphorus atom to give Me~2~P–PMe^−^ plus ethylene, were calculated at the G3(MP2)‐RAD(+) level. The rate constant for this mechanism (k = 1.1 × 10^13^ L mol^−1^ s^−1^ at 25°C) is seven orders of magnitude greater than that for the previously studied mechanism involving attack at carbon. Experimental investigations with 1‐phenylphosphirane gave consistent results: Treatment with LiPMePh yielded no detectable polymer, and quenching with MeI gave the known diphosphine (R*, R*)‐(±)/(R*, S*)‐MePhP‐‐PMePh. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:178–181, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20405

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