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Tavs reactions of o-halobenzaldimines with ethyl diphenylphosphinite. Synthesis and crystal structure of a bis(phosphine oxide)

Tavs reactions of o-halobenzaldimines with ethyl diphenylphosphinite. Synthesis and crystal structure of a bis(phosphine oxide)
Tavs reactions of o-halobenzaldimines with ethyl diphenylphosphinite. Synthesis and crystal structure of a bis(phosphine oxide)
The reactions of a series of o-halobenzaldimines with ethyl diphenylphosphinite in ethanol, in the presence of nickel(II), proceed with a coordination template-assisted Tavs phosphonylation at the carbon to which the halogen was attached and addition of diphenylphosphine oxide to the imino bond, to form a bis(phosphine oxide), the structure of which has been confirmed by X-ray crystallography. Carrying out the reaction in acetonitrile, in the presence of copper(I) iodide, results only in a Tavs replacement of halogen by phosphorus, to give an o-diphenylphosphinylaryl imine.
group-15 onium salts, trialkyl phosphites, aryl halides, arsonium
242-245
Allen, David W.
4cbcd21b-4bb9-40e8-baa9-27b1b3e5a7b2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Allen, David W.
4cbcd21b-4bb9-40e8-baa9-27b1b3e5a7b2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Allen, David W., Coles, Simon J. and Hursthouse, Michael B. (2005) Tavs reactions of o-halobenzaldimines with ethyl diphenylphosphinite. Synthesis and crystal structure of a bis(phosphine oxide). Heteroatom Chemistry, 16 (3), 242-245. (doi:10.1002/hc.20117).

Record type: Article

Abstract

The reactions of a series of o-halobenzaldimines with ethyl diphenylphosphinite in ethanol, in the presence of nickel(II), proceed with a coordination template-assisted Tavs phosphonylation at the carbon to which the halogen was attached and addition of diphenylphosphine oxide to the imino bond, to form a bis(phosphine oxide), the structure of which has been confirmed by X-ray crystallography. Carrying out the reaction in acetonitrile, in the presence of copper(I) iodide, results only in a Tavs replacement of halogen by phosphorus, to give an o-diphenylphosphinylaryl imine.

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More information

Published date: 2005
Keywords: group-15 onium salts, trialkyl phosphites, aryl halides, arsonium

Identifiers

Local EPrints ID: 20701
URI: https://eprints.soton.ac.uk/id/eprint/20701
PURE UUID: af1eb795-85b6-4443-9a82-34eccd2507ed
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 28 Feb 2006
Last modified: 06 Jun 2018 12:54

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Contributors

Author: David W. Allen
Author: Simon J. Coles ORCID iD

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