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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 12
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Original Articles

Synthesis and Reactivity of the New Chiral Silylphosphite Esters {(+)-O, O-Dimethyl-L-tartrate}POSiR3 (R3 = Ph3, tBuMe2, Et3)

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Pages 1643-1650 | Received 18 Dec 1992, Published online: 23 Sep 2006

References

  • Wozniak , L. and Chojnowski , J. 1989 . Tetrahedron , 45 : 2465 and references therein.
  • Abramov , V. S. 1954 . Dokl. Acad. Nauk SSSR , 95 : 991
  • Hildebrand , R. L. , ed. 1983 . “The Role of Phosphonates in Living Systems” , Boca Raton, Florida : CRC Press .
  • Sum , V. , Davies , A. J. and Kee , T. P. 1992 . J. Chem. Soc., Chem. Commun. , : 1771
  • Wink , D. J. , Kwok , T. J. and Yee , A. 1990 . Inorg. Chem. , 29 : 5006
  • In some runs, the isolated samples of 1 and 2 appear to be undergoing an exchange process as judged from 1H NMR. Thus broad signals are observed at room temperature but upon cooling a sample of 1 to ∞. −50° the resonances sharpen and take on the coupling patterns expected for a static structure. We have not investigated the cause of this occasional onset of fluxionality. We have never observed the same behavior with the silylphosphites 3–5
  • For each of 3–5, 1H NMR spectroscopy reveals that one of the methine hydrogens couples more strongly to phosphorus. We assign this methine as that which is cisoid to the siloxo group (see scheme 2). 10 In a similar fashion, the carbonyl carbon atoms that are cisoid to the siloxo group also couple more strongly to phosphorus.
  • Fontal , B. and Goldwhite , H. 1966 . Tetrahedron , 22 : 3275
  • Greene , N. and Kee , T. P. following paper in this issue.
  • Robert , J. B. and Weichmann , H. 1978 . J. Org. Chem. , 43 : 3031

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