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Updated: Jun 8, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Oxaphosphiranes: isolable phosphorus-containing epoxide rings
Niklas Volk1, Antonio García Alcaraz2, Selvakumar Balasubramaniam1
1Institut für Anorganische Chemie, der Rheinischen Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121, Bonn, Germany. r.streubel@uni-bonn.de.
Abstract:
Combining different heteroatoms in an epoxide-type ring having Lewis basic and acidic characteristics is challenging as it creates an increasing number of polar bonds and high ring strain energy. The first examples of isolable oxaphosphiranes, i.e., epoxide rings with a phosphorus atom, have been synthesized using a facile and effective protocol starting from [pentacarbonyl{dichloro(trityl)phosphane}molybdenum(0)] (trityl = CPh3), tert-butyllithium and commercially available fluorinated benzaldehydes. Reactions with various acids and bases will be described. Theoretical results unveil a singlet carbene-like FMO situation at phosphorus in oxaphosphirane, which is used to explain reaction mechanisms.
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