Stabilization and Transfer of the Transient [Mes∗P4]- Butterfly Anion Using BPh3

Jaap E. Borger; Andreas W. Ehlers; Martin Lutz; J. Chris Slootweg; Koop Lammertsma

doi:10.1002/anie.201508916

Stabilization and Transfer of the Transient [Mes∗P₄]^- Butterfly Anion Using BPh₃

Jaap E. Borger
, Andreas W. Ehlers
, Martin Lutz
, J. Chris Slootweg
, Koop Lammertsma

Chemical Sciences

Vrije Universiteit Amsterdam
Utrecht University

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

The transient bicyclo[1.1.0]tetraphosphabutane anion, generated from white phosphorus (P₄) and Mes∗Li (Mes∗=2,4,6-tBu₃C₆H₂), can be trapped by BPh₃ in THF. This Lewis acid stabilized anion can be used as an [RP₄]^- transfer agent, reacting cleanly with neutral Lewis acids (B(C₆F₅)₃, BH₃, and W(CO)₅) to afford unique singly and doubly coordinated butterfly anions, and with the trityl cation to form a neutral, nonsymmetrical, all-carbon-substituted P₄derivative. This reaction path enables a simple, stepwise functionalization of white phosphorus. Trap and transfer: The bicyclo[1.1.0]tetraphosphabutane anion (see scheme, center), generated from P₄ and Mes∗Li (Mes∗=2,4,6-tBu₃C₆H₂), can be trapped by BPh₃ in THF. The anion can be used as an [RP₄]^- transfer agent, reacting with neutral Lewis acids (B(C₆F₅)₃, BH₃, and W(CO)₅) to afford unique singly and doubly coordinated butterfly anions and with the trityl cation to form a neutral, nonsymmetrical P₄ derivative.

Original language	English
Pages (from-to)	613-617
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	2
DOIs	https://doi.org/10.1002/anie.201508916
Publication status	Published - 11 Jan 2016

Keywords

Lewis acids
anions
boranes
organophosphorus compounds
phosphorus

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201508916

Cite this

@article{6a1a0d1c456f4278bea3897ec1ae23bd,

title = "Stabilization and Transfer of the Transient [Mes∗P4]- Butterfly Anion Using BPh3",

abstract = "The transient bicyclo[1.1.0]tetraphosphabutane anion, generated from white phosphorus (P4) and Mes∗Li (Mes∗=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. This Lewis acid stabilized anion can be used as an [RP4]- transfer agent, reacting cleanly with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions, and with the trityl cation to form a neutral, nonsymmetrical, all-carbon-substituted P4derivative. This reaction path enables a simple, stepwise functionalization of white phosphorus. Trap and transfer: The bicyclo[1.1.0]tetraphosphabutane anion (see scheme, center), generated from P4 and Mes∗Li (Mes∗=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. The anion can be used as an [RP4]- transfer agent, reacting with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions and with the trityl cation to form a neutral, nonsymmetrical P4 derivative.",

keywords = "Lewis acids, anions, boranes, organophosphorus compounds, phosphorus",

author = "Borger, \{Jaap E.\} and Ehlers, \{Andreas W.\} and Martin Lutz and Slootweg, \{J. Chris\} and Koop Lammertsma",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

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AU - Borger, Jaap E.

AU - Ehlers, Andreas W.

AU - Lutz, Martin

AU - Slootweg, J. Chris

AU - Lammertsma, Koop

PY - 2016/1/11

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N2 - The transient bicyclo[1.1.0]tetraphosphabutane anion, generated from white phosphorus (P4) and Mes∗Li (Mes∗=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. This Lewis acid stabilized anion can be used as an [RP4]- transfer agent, reacting cleanly with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions, and with the trityl cation to form a neutral, nonsymmetrical, all-carbon-substituted P4derivative. This reaction path enables a simple, stepwise functionalization of white phosphorus. Trap and transfer: The bicyclo[1.1.0]tetraphosphabutane anion (see scheme, center), generated from P4 and Mes∗Li (Mes∗=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. The anion can be used as an [RP4]- transfer agent, reacting with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions and with the trityl cation to form a neutral, nonsymmetrical P4 derivative.

AB - The transient bicyclo[1.1.0]tetraphosphabutane anion, generated from white phosphorus (P4) and Mes∗Li (Mes∗=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. This Lewis acid stabilized anion can be used as an [RP4]- transfer agent, reacting cleanly with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions, and with the trityl cation to form a neutral, nonsymmetrical, all-carbon-substituted P4derivative. This reaction path enables a simple, stepwise functionalization of white phosphorus. Trap and transfer: The bicyclo[1.1.0]tetraphosphabutane anion (see scheme, center), generated from P4 and Mes∗Li (Mes∗=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. The anion can be used as an [RP4]- transfer agent, reacting with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions and with the trityl cation to form a neutral, nonsymmetrical P4 derivative.

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