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Original Articles

REACTIONS OF 1,2-OXAPHOSPHOLENE-2- OXIDES 5.1 CONSEQUENCES OF REDUCTION

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Pages 15-20 | Received 05 Apr 1989, Published online: 04 Oct 2006

References

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  • 1988 . PhD Dissertation of MM University of Cincinnati . Taken from the
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  • Macomber , R. S. , Krudy , G. A. , Seff , K. and Diaz-Miron , L. E. R. 1983 . J. Org. Chem. , 48 : 1425
  • Macomber , R. S. and Krudy , G. A. 1978 . J. Org. Chem. , 43 : 4656
  • Macomber , R. S. and Krudy , G. A. 1981 . J. Org. Chem. , 46 : 4028
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  • The ir spectrum of 3exhibits weak broad bands for the P=O group (1190cm−1) and P–H (2300–2400 cm−1). In addition, there is a weak doublet in the 1H spectrum at δ 7.54 (J = 510 Hz). This indicates that 3 exists in tautomeric equilibrium with 4. The relative amounts of these tautomers is nearly equal, judging from the intensities of their gem-dimethyl singlets.
  • For comparison, the 1H nmr spectrum of 1a shows the following signals: δ 1.58 (s, 3H), 1.67 (s, 3H), 6.18 (dd, J = 33.5 and 8.2 Hz, 1H), 7.08 (dd, J = 40.1 and 8.2 Hz, 1H), 7.4–8.O (m, 5H).1
  • Lambert , J. B. , Shurvell , H. F. , Verbit , L. , Cooks , R. G. and Stout , G. H. 1976 . Organic Structural Analysis , 291 New York : McMillan .
  • Verkade , J. G. , King , R. W. and Heitsch , C. W. 1964 . Inorg. Chem. , 3 : 384 The fact that the B-H protons in 7 were not observed in its 1H nmr spectrum is not without precedent. Although the borane hydrogens in (CH3O)3PBH3 and several bicyclic phosphite borane complexes appear around δ -0.3
  • Frisch , M. A. , Heal , H. G. , Mackle , H. and Madden , I. O. 1965 . J. Chem. Soc. , : 899 those in triphenylphosphineborane complex were not observable
  • Verkade , J. G. and Milbrath , D. S. 1977 . J. Am. Chem. Soc. , 99 : 2457 See, for example
  • Elegant , L. , Gal , J.-F. , Jouany , C. and Jugie , G. 1978 . Can. J. Chem. , 56 : 857 and references therein.
  • Pelter , A. , Rosser , R. and Mills , S. 1981 . Chem. Commun. , : 1014
  • Pasto , D. J. 1964 . J. Am. Chem. Soc. , 86 : 3039
  • Nurtdinov , S. K. , Ismagilov , N. M. , Kahrutdinovaand , R. A. and Zybova , T. V. 1983 . J. Gen. Chem. USSR , 53 : 923
  • Segall , Y. , Granoth , I. and Kalir , A. 1974 . Chem. Commun. k , : 501 See, for example
  • Quin , L. D. , Hughes , A. N. , Lawson , H. F. and Good , A. L. 1983 . Tetrahedron , 39 : 401
  • Marinetti , A. and Mathey , F. 1985 . J. Am. Chem. Soc. , 107 : 4700
  • Apparently the POH and COH protons in 3 readily exchange in CDCl3 solution, becoming equivalent on the 300 MHz time scale.
  • Brown , R. A. and Dobson , G. R. 1972 . Inorg. Chem. Acta , 6 : 66

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