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Facile one-pot synthesis of functionalized organophosphonate esters via ketone insertion into bulky arylphosphites

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Abstract

The reaction of phosphorus trichloride with 2,6-diisopropyl phenol in the presence of LiCl under reflux conditions for 24 h produces a mixture of (ArO)PCl2 and (ArO)2PCl (Ar = 2,6-iPr2C6H3). The hydrolysis of the aryloxy compounds in acetone/H2O results in the formation of two novel phosphonate ester derivatives [(ArO)P(O)(OH)(CMe2OH)] (1) and [(ArO)2P(O)(CMe2OH)] (2), respectively in a moderate yield. The title compounds have presumably formed via acetone insertion to the P-H bonds of (ArO)P(O)(H)(OH) and (ArO)2P(O)(H), respectively, in the presence of HCl produced during the hydrolysis. Compounds 1 and 2 have been characterized by elemental analysis, and ESI-mass, Infrared and NMR spectroscopic techniques. Further, solid state structures of 1 and 2 have been established by single crystals X-ray diffraction studies.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076, India

    Ramaswamy Murugavel & Subramaniam Kuppuswamy

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  1. Ramaswamy Murugavel
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  2. Subramaniam Kuppuswamy
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Correspondence to Ramaswamy Murugavel.

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Murugavel, R., Kuppuswamy, S. Facile one-pot synthesis of functionalized organophosphonate esters via ketone insertion into bulky arylphosphites. J Chem Sci 120, 131–136 (2008). https://doi.org/10.1007/s12039-008-0015-2

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