Experimental and quantum chemical studies of 2-phosphinylphenol derivatives

Article abstract of DOI:10.1080/10426509908546316

Carbon-oxygen bonds ortho to a phosphoryl group in triarylphosphine oxides undergo cleavage when the oxides are either fused with potassium hydroxide or treated with potassium tert-butoxide in refluxing toluene, presumably through a nucleophilic addition-elimination mechanism. Thus, bis(2-hydroxyphenyl)phenylphosphine oxide is produced along with the expected 2-phenoxyphenyl(phenyl)phosphinic acid from 10-phenyl-10H-phenoxaphosphine 10-oxide. The latter starting material is also produced, together with bis(2-hydroxyphenyl)phenylphosphine oxide, when bis(2-methoxyphenyl)phenylphosphine oxide is fused with potassium hydroxide. Fusion of bis(2-methoxyphenyl)phenylphosphine oxide with sodium hydroxide, however, yields 2-hydroxyphenyl(phenyl)phosphinic acid. Ab initio quantum chemical studies confirm that the downfield ³¹P chemical shift that is observed in 2-phosphinylphenols is due to hydrogen bonding to the phosphoryl group.

Full text of DOI:10.1080/10426509908546316

This article was downloaded by: [Florida International University]
On: 22 December 2014, At: 02:38
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number:
1072954 Registered office: Mortimer House, 37-41 Mortimer
Street, London W1T 3JH, UK
Phosphorus, Sulfur, and
Silicon and the Related
Elements
Publication details, including instructions
for authors and subscription information:
http://www.tandfonline.com/loi/gpss20
Experimental and
Quantum Chemical
Studies of 2-
Phosphinylphenol
Derivatives
Jack B. Levy , Steven B. Sutton & Ronald
E. Olsen
a Department of Chemistry , University
of North Carolina at Wilmington
Wilmington , NC 28403, USA
b Department of Chemistry , University
of North Carolina at Wilmington
Wilmington , NC 28403, USA
c Department of Chemistry , University
of North Carolina at Wilmington
Wilmington , NC 28403, USA
Published online: 17 Mar 2008.
To cite this article: Jack B. Levy , Steven B. Sutton & Ronald E. Olsen
(1999) Experimental and Quantum Chemical Studies of 2-Phosphinylphenol
Derivatives, Phosphorus, Sulfur, and Silicon and the Related Elements,
144:1, 601-604, DOI: 10.1080/10426509908546316

To link to this article: http://dx.doi.org/10.1080/10426509908546316
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of
all the information (the “Content”) contained in the publications
on our platform. However, Taylor & Francis, our agents, and our
licensors make no representations or warranties whatsoever as
to the accuracy, completeness, or suitability for any purpose of
the Content. Any opinions and views expressed in this publication
are the opinions and views of the authors, and are not the views
of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified
with primary sources of information. Taylor and Francis shall not
be liable for any losses, actions, claims, proceedings, demands,
costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with,
in relation to or arising out of the use of the Content.
This article may be used for research, teaching, and private
study purposes. Any substantial or systematic reproduction,
redistribution, reselling, loan, sub-licensing, systematic supply,
or distribution in any form to anyone is expressly forbidden.
Terms & Conditions of access and use can be found at http://
www.tandfonline.com/page/terms-and-conditions