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Interaction of PH3 with acetaldehyde in aqueous media and chemistry of [HO(Me)CH]4PCl

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Abstract

The known phosphonium chloride [HO(Me)CH]4PCl was prepared at ambient conditions from PH3 and acetaldehyde in aqueous HCl, and characterized by elemental analysis and 1H and 31{1H} NMR spectroscopy. Attempts to obtain the tertiary phosphine [HO(Me)CH]3P via reaction of [HO(Me)CH]4PCl with Na2SO3 or Et3N in aqueous media under Ar revealed that [HO(Me)CH]3P is unstable and equilibrates with the secondary phosphine [HO(Me)CH]2PH and acetaldehyde. A 1:4 reaction of [HO(Me)CH]4PCl with NaHSO3 at room temperature under Ar affords first the oxide [HO(Me)CH]2P(O)H and then the phosphinic acid [HO(Me)CH]2P(O)OH. A 1:1 reaction of [HO(Me)CH]4PCl with Na2S2O3 affords the sulfide [HO(Me)CH]3PS. 31{1H} and 1H NMR data for all the (α-hydroxyethyl)phosphorus species are reported for the first time.

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Authors and Affiliations

  1. Department of Chemistry, University of British Columbia, Vancouver, British Columbia, V6T 1Z1, Canada

    D. V. Moiseev & B. R. James

  2. Department of Organic Chemistry, Lobachevsky State University of Nizhny Novgorod, pr. Gagarina 23, Nizhny Novgorod, 603950, Russia

    D. V. Moiseev & A. V. Gushchin

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  1. D. V. Moiseev
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  2. B. R. James
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  3. A. V. Gushchin
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Correspondence to D. V. Moiseev.

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Original Russian Text © D.V. Moiseev, B.R. James, A.V. Gushchin, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 2, pp. 198–205.

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Moiseev, D.V., James, B.R. & Gushchin, A.V. Interaction of PH3 with acetaldehyde in aqueous media and chemistry of [HO(Me)CH]4PCl. Russ J Gen Chem 83, 252–259 (2013). https://doi.org/10.1134/S1070363213020047

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  • DOI: https://doi.org/10.1134/S1070363213020047

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