S. N. Arbuzova, N. K. Gusarova, M. V. Bogdanova, I. A. Ushakov, A. G. Mal'kina, B. A. Trofimov, “Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts”, Mendeleev Commun., 17:6 (2007), 325

Abstract: Bis(2-phenylethyl)phosphine oxide and sulfide and bis[2-(2-pyridyl)ethyl]phosphine sulfide add easily (LiOH–THF, 28–30°C) to 4-hydroxy-4-methyl-2-pentynenitrile to give regio- and stereoselectively 3-substituted (Z)-4-hydroxy-4-methyl-2-pentenenitriles in 82–91% yield; the latter, upon heating (58–60°C) in the presence of LiOH in THF, rearrange cleanly to the corresponding 3-cyano-2-propen-1-yl phosphinates and phosphinothioates (isolated yields of 82–86%).

This publication is cited in the following 8 articles:

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Biswajit Deb, Bhaskar Jyoti Sarmah, Bibek Jyoti Borah, Dipak Kumar Dutta, “Synthesis, characterisation and thermal studies of ruthenium(II) carbonyl complexes of functionalised tripodal phosphine chalcogen donor ligands, [CH3C(CH2P(X)Ph2)3], where X=Se, S, O”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 72:2 (2009), 339
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Svetlana N. Arbuzova, Nina K. Gusarova, Maria V. Bogdanova, Igor A. Ushakov, Anastasiya G. Mal'kina, Boris A. Trofimov, “ChemInform Abstract: Nucleophilic Addition of Secondary Phosphine Chalcogenides to α,β‐Acetylenic γ‐Hydroxy Acid Nitriles and a Rearrangement of the Adducts.”, ChemInform, 39:30 (2008)
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