Synthesis of polyols bearing phosphonate groups. Part II: Epoxides used as starting materials

Article abstract of DOI:10.1080/10426500008042092

Three epoxyphosphonates were prepared. These compounds have the following general formula: CH₂(O)C(R)-Z-PO(OCH₂CH₃)₂with (II): R=H, Z=CH₂; (V): R=H, Z=CH₂O(CH₂)₃S(CH₂)₃; (VI): R=CH₃. (II) is obtained by epoxidation of diethyl allylphosphonate by hydrogen peroxide in the presence of benzonitrile with a yield superior to 60%. (V) is obtained by photoaddition of HS(CH₂)₃PO(OCH₂CH₃)₂ to allyl glycidyl ether CH₂(O)CH CH₂-O-CH₂CH=CH₂ with a high yield. (VI) is obtained by addition of diethyl hydrogenophosphonate HPO(OCH₂CH₃)₂ to 1-chloropropan-2-one CH₃C(O) CH₂Cl with a yield of 80%. These epoxides then lead to polyols bearing a phosphonate group by ring opening with diethanolamine (HOCH₂CH₂)₂NH: (HOCH₂CH₂)₂NCH₂C(OH)(R)-Z-PO(OCH₂CH₃)₂, with (VII): R=H, Z=CH₂; (VIII): R=H, Z=CH₂O(CH₂)₃S(CH₂)₃; (IX): R= CH₃. This reaction appears to be an easy method without any need for solvent or catalyst, and could be of industrial interest.

Full text of DOI:10.1080/10426500008042092

This article was downloaded by: [Temple University Libraries]
On: 22 November 2014, At: 17:24
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
SYNTHESIS OF POLYOLS
BEARING PHOSPHONATE
GROUPS. PART II: EPOXIDES
USED AS STARTING MATERIALS
B. Boutevin a , Y. Hervaud a , G. Mouledous a & R.
Vera a
a UPRESA 5076 CNRS, Luboratoire de Chimie
Macromoléculaire , Ecole Nationale Supérieure de
Chimie de Montpellier -8, Rue de l'Ecole Normale,
34296, Montpellier Cedex 5, France
Published online: 04 Oct 2006.
To cite this article: B. Boutevin , Y. Hervaud , G. Mouledous & R. Vera (2000)
SYNTHESIS OF POLYOLS BEARING PHOSPHONATE GROUPS. PART II: EPOXIDES USED
AS STARTING MATERIALS, Phosphorus, Sulfur, and Silicon and the Related Elements,
161:1, 9-27, DOI: 10.1080/10426500008042092
To link to this article: http://dx.doi.org/10.1080/10426500008042092
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