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Reaction of polyperoxides with triphenylphosphine

Jayanthi, Saraswathyammal and Kishore, Kaushal (1997) Reaction of polyperoxides with triphenylphosphine. In: Journal of Polymer Science Part A: Polymer Chemistry, 35 (7). pp. 1167-1172.

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The triphenylphosphine deoxygenation of the polyperoxides, poly(styrene peroxide), poly(methyl methacrylate peroxide), and poly(alpha-methylstyrene peroxide) proceed via the phosphorane intermediates, which in the presence of moisture hydrolyze to give the respective diols. At higher temperatures and under dry conditions the phosphorane decomposes into epoxide and triphenylphosphine oxide. The reaction has been studied by H-1-, C-13-, and P-31-NMR spectroscopy. The results obtained are consistent with a concerted insertion of the biphile, triphenylphosphine, into the peroxy bond and this reaction pathway seems to be new as far as the chemistry of polyperoxides is concerned. Though the aim of this investigation was to test the selective deoxygenation of polyperoxide by triphenylphosphine as a method of preparing polyethers, it turned out to be a fruitful method of synthesis of stereospecific diols. (C) 1997 John Wiley & Sons, Inc.

Item Type: Journal Article
Publication: Journal of Polymer Science Part A: Polymer Chemistry
Publisher: John Wiley and Sons
Additional Information: Copyright of this article belongs to John Wiley and Sons.
Keywords: deoxygenation;polyperoxides;biphile;concerted insertion;NMR spectroscopy
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 30 Jun 2011 13:45
Last Modified: 30 Jun 2011 13:45
URI: http://eprints.iisc.ac.in/id/eprint/38378

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