NMR STUDY OF PHOSPHORUS-CARBON AND PHOSPHORUS-NITROGEN BONDS IN ALKYL-AND MONO-N-SUBSTITUTED AMINOTRIARYLPHOSPHONIUM SALTS

References

• September 1986 . September , Bonn, , Germany Part of this work was presented at the International Conference on Phosphorus Chemistry
   Google Scholar
• Hendrickson , J. B. , Maddox , M. L. , Sims , J. J. and Kaesz , H. D. 1964 . Tetrahedron , 20 : 449
   Web of Science ®Google Scholar
• Griffin , C. E. and Gordon , M. 1965 . J. Organomet. Chem. , 3 : 414
   Google Scholar
• Grim , S. O. , McFarlane , W. , Davidoff , E. F. and Marks , T. J. 1966 . J. Phys. Chem. , 70 : 581
   Web of Science ®Google Scholar
• Albright , T. A. , Freeman , W. J. and Schweizer , E. E. 1975 . J. Am. Chem. Soc. , 97 : 2942
   Web of Science ®Google Scholar
• Gray , G. A. , Cremer , S. E. and Marsi , K. L. 1976 . J. Am. Chem. Soc. , 98 : 2109
   Web of Science ®Google Scholar
• Johnson , A. W. 1993 . Ylides and Imines of Phosphorus , New York : John Wiley & Sons, Inc. .
   Google Scholar
• Dixon , D. A. in Reference 7
   Google Scholar
• Stothers , J. B. 1972 . Carbon-13 NMR Spectroscopy , New York : Academic Press .
   Google Scholar
• 70 – 71 . Reference 9
   Google Scholar
• Albright , T. A. , Freeman , W. J. and Schweizer , E. E. 1975 . J. Am. Chem. Soc. , 97 : 940
   Web of Science ®Google Scholar
• Luttke , W. and Wilhelm , K. 1965 . Agnew. Chem. Internat. Edit. , 4 : 875
   Web of Science ®Google Scholar
• Lumbroso , H. , Cure , J. and Bestmann , H. J. 1978 . J. Organomet. Chem. , 161 : 347
   Google Scholar
• Grim , S. O. , McFarlane , W. and Marks , T. F. 1967 . Chem. Commun. , : 1191
   Web of Science ®Google Scholar
• Mann , B. E. 1974 . Advances in Organometallic Chemistry , Edited by: Stone , F. G. A. and West , R. 135 – 213 . New York : Academic Press . For a review, see
   Google Scholar
• Smith , G. W. 1963 . J. Chem. Phys. , 39 : 2031
   Web of Science ®Google Scholar
• 2JPH is usually negative in alkylphosphonium salts, e.g., Ph3∗∗∗P+CH3 I- (-13.2 Hz)18 and (CH3)4∗∗∗P+ I- (14.6 Hz).19 With the increase in s character of the C—H bonds, the numerical values of 2JPH decrease, i.e., increase in positive direction; see, e.g., Ph3∗∗∗P+CH2OH Cl- (0.0 Hz)20 and Ph3∗∗∗P+CH2OCH3 Cl- (4.0 Hz).2 Actually, (CH3)3 P═CH2 ylid has 2JPH of +6.5 Hz.19 The ylid 13C—H coupling is 149 Hz, which calculates to 29.8% s character in its carbon orbitals according to the method of Juan and Gutowsky.21
   Google Scholar
• Manatt , S. L. , Juvinall , G. L. , Wagner , R. I. and Elleman , D. D. 1966 . J. Am. Chem. Soc. , 88 : 2689
   Web of Science ®Google Scholar
• Schmidbaur , H. , Buchner , W. and Scheutzow , D. 1973 . Chem. Ber. , 106 : 1251
   Google Scholar
• Allen , D. W. , Millar , I. T. and Tebby , J. C. 1968 . Tetrahedron Lett. , : 745
   Google Scholar
• Juan , C. and Gutowsky , H. S. 1962 . J. Chem. Phys. , 37 : 2198 13 C—H coupling has been related to the amount of s character in the carbon orbitals: %s character = J13C—H (in Hz)/5; see
   Web of Science ®Google Scholar
• Gallagher , M. J. 1968 . Aust. J. Chem. , 21 : 1197 For a review of 2JPH coupling constants in phosphonium salts, see
   Web of Science ®Google Scholar
• Weigert , F. J. and Roberts , J. D. 1973 . Inorg. Chem. , 12 : 314
   Google Scholar
• Karabatsos , G. J. , Graham , J. D. and Vane , F. M. 1962 . J. Am. Chem. Soc. , 84 : 37
   Google Scholar
• This is consistent with the transylidation between Ph3P═CH2 and Ph3PCH2C(CH3)3 I- which occurs quantitatively in favor of the formation of Ph3P═CHC(CH3),26 indicating its greater stability due to the more effective ylid bond formation
   Google Scholar
• Seyferth , D. and Singh , G. 1965 . J. Am. Chem. Soc. , 87 : 4156
   Google Scholar
• Fritchie, Jr. , C. J. 1966 . Acta Cryst. , 20 : 107
   Google Scholar
• Singh , G. and Zimmer , H. 1965 . J. Org. Chem. , 30 : 313
   PubMedGoogle Scholar
• 415 Reference 7
   Google Scholar
• Koeppl , G. W. , Sagatys , D. S. , Krishnamurty , G. S. and Miller , S. I. 1967 . J. Am. Chem. Soc. , 89 : 3396
   Google Scholar
• Bushweller , C. H. and O'Neil , J. W. 1970 . ibid. , 92 : 2159
   Google Scholar
• Dewar , M. J. S. and Jennings , W. B. 1971 . ibid. , 93 : 401
   Google Scholar
• Anderson , J. E. , Griffith , D. L. and Roberts , J. D. 1969 . J. Am. Chem. Soc. , 91 : 6371
   Google Scholar
• Dewar , M. J. S. and Jennings , W. B. 1973 . J. Am. Chem. Soc. , 95 : 1562
   Google Scholar
• Bushweller , C. H. 1992 . Acyclic Organonitrogen Sterodynamics , Edited by: Lambert , J. B. and Takeuchi , Y. 1 – 55 . New York : VCH Publishers, Inc. . For excellent recent reviews on the stereodynamics of amines and hydrazines see:
   Google Scholar
• Nelsen , S. F. ibid. , 89 – 121 .
   Google Scholar
• Doddrell , D. M. , Pegg , D. T. and Bendall , M. R. 1982 . J. Magn. Reson. , 48 : 323
   Web of Science ®Google Scholar
• Singh , G. 1987 . J. Org. Chem. , 52 : 1647
   Google Scholar
• Horner , L. and Moser , H. 1966 . Chem. Ber. , 99 : 2789
   Google Scholar
• Singh , G. and Zimmer , H. 1967 . Organomet. Chem. Rev. , 2 : 279 For original references, see
   Google Scholar
• Appel , R. and Hauss , A. 1961 . Z. Anorg. Allegem. Chem. , 311 : 290
   Web of Science ®Google Scholar
• Zimmer , H. and Singh , G. 1964 . J. Org. Chem. , 29 : 3412
   Web of Science ®Google Scholar
• Main , P. , Lessinger , L. , Woolfson , M. W. , Germain , G. and Declerg , J. P. 1978 . MULTAN 78: A System of Computer Programs for the Automatic Solution of Crystal Structures from X-ray Diffraction Data Louvain-la-Neuve, , England
   Google Scholar