Direct synthesis of trifluoromethyl decorated diphenylphosphites. Unusual non-bonded structural features in bis-[(2-trifluoromethyl)phenylphosphite: [2-(CF3)C6H4]2P(O)H]

Sylvie Pailloux; Eileen N. Duesler; Karen Ann Smith; Robert T. Paine; John R. Klaehn; Michael E. McIlwain

doi:10.1080/10241220903177071

Direct synthesis of trifluoromethyl decorated diphenylphosphites. Unusual non-bonded structural features in bis-[(2-trifluoromethyl)phenylphosphite: [2-(CF₃)C₆H₄]₂P(O)H]

Sylvie Pailloux
, Eileen N. Duesler
, Karen Ann Smith
, Robert T. Paine
, John R. Klaehn
, Michael E. McIlwain

Materials, Manufacturing, & Bioenergy S&T

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

3 Scopus citations

Abstract

A direct, Grignard reagent-based route for the syntheses of [2-(CF₃)C₆H₄]₂P(O)H(1) and [3,5-(CF₃)₂C₆H₃]₂P(O)H (2) has been developed and the isolation and characterization of these crystalline reagents is described. The crystal structures for 1 and 2 were determined and the structure of 1 reveals unexpected close non-bonded interaction between F-atoms of one CF₃ group and the back-side of the central phosphorus atom.

Original language	English
Pages (from-to)	207-220
Number of pages	14
Journal	Main Group Chemistry
Volume	8
Issue number	3
DOIs	https://doi.org/10.1080/10241220903177071
State	Published - Sep 2009

Keywords

Diphenylphosphite
Grignard reagent
Non-bonded phosphorus-fluorine interactions
Trifluoromethyl group
X-ray crystal structures

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10.1080/10241220903177071

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title = "Direct synthesis of trifluoromethyl decorated diphenylphosphites. Unusual non-bonded structural features in bis-[(2-trifluoromethyl)phenylphosphite: [2-(CF3)C6H4]2P(O)H]",

abstract = "A direct, Grignard reagent-based route for the syntheses of [2-(CF3)C6H4]2P(O)H(1) and [3,5-(CF3)2C6H3]2P(O)H (2) has been developed and the isolation and characterization of these crystalline reagents is described. The crystal structures for 1 and 2 were determined and the structure of 1 reveals unexpected close non-bonded interaction between F-atoms of one CF3 group and the back-side of the central phosphorus atom.",

keywords = "Diphenylphosphite, Grignard reagent, Non-bonded phosphorus-fluorine interactions, Trifluoromethyl group, X-ray crystal structures",

author = "Sylvie Pailloux and Duesler, \{Eileen N.\} and Smith, \{Karen Ann\} and Paine, \{Robert T.\} and Klaehn, \{John R.\} and McIlwain, \{Michael E.\}",

year = "2009",

month = sep,

doi = "10.1080/10241220903177071",

language = "English",

volume = "8",

pages = "207--220",

journal = "Main Group Chemistry",

issn = "1024-1221",

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TY - JOUR

T1 - Direct synthesis of trifluoromethyl decorated diphenylphosphites. Unusual non-bonded structural features in bis-[(2-trifluoromethyl)phenylphosphite

T2 - [2-(CF3)C6H4]2P(O)H]

AU - Pailloux, Sylvie

AU - Duesler, Eileen N.

AU - Smith, Karen Ann

AU - Paine, Robert T.

AU - Klaehn, John R.

AU - McIlwain, Michael E.

PY - 2009/9

Y1 - 2009/9

N2 - A direct, Grignard reagent-based route for the syntheses of [2-(CF3)C6H4]2P(O)H(1) and [3,5-(CF3)2C6H3]2P(O)H (2) has been developed and the isolation and characterization of these crystalline reagents is described. The crystal structures for 1 and 2 were determined and the structure of 1 reveals unexpected close non-bonded interaction between F-atoms of one CF3 group and the back-side of the central phosphorus atom.

AB - A direct, Grignard reagent-based route for the syntheses of [2-(CF3)C6H4]2P(O)H(1) and [3,5-(CF3)2C6H3]2P(O)H (2) has been developed and the isolation and characterization of these crystalline reagents is described. The crystal structures for 1 and 2 were determined and the structure of 1 reveals unexpected close non-bonded interaction between F-atoms of one CF3 group and the back-side of the central phosphorus atom.

KW - Diphenylphosphite

KW - Grignard reagent

KW - Non-bonded phosphorus-fluorine interactions

KW - Trifluoromethyl group

KW - X-ray crystal structures

UR - https://www.scopus.com/pages/publications/75349103053

U2 - 10.1080/10241220903177071

DO - 10.1080/10241220903177071

M3 - Article

AN - SCOPUS:75349103053

SN - 1024-1221

VL - 8

SP - 207

EP - 220

JO - Main Group Chemistry

JF - Main Group Chemistry

IS - 3

ER -

Direct synthesis of trifluoromethyl decorated diphenylphosphites. Unusual non-bonded structural features in bis-[(2-trifluoromethyl)phenylphosphite: [2-(CF₃)C₆H₄]₂P(O)H]

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