8
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

CONFORMATIONAL ANALYSIS OF DIALKYL (2,5-DIALKYL PYRROLIDIN-2-YL)PHOSPHONATES AND DIETHYL(2,5,5-TRIMETHYL PYRROLIDIN-2-YL)PHOSPHONATE BY X-RAY ANALYSIS, NMR AND FORCE FIELD CALCULATIONS

, , , , &
Pages 143-153 | Received 21 Sep 1995, Accepted 17 Oct 1995, Published online: 04 Oct 2006

References

  • Roubaud , V. , Le Moigne , F. , Mercier , A. and Tordo , P. 1994 . Phosphorus Sulfur , 86 : 39
  • Mercier , A. , Berchadsky , Y. , Pietri , S. and Tordo , P. 1991 . Tetrahedron Lett. , 32 : 2125
  • Fréjaville , C. , Karoui , H. , Le Moigne , F. , Culcasi , M. , Pietri , S. and Tordo , P. French Pat. (n° PV 9308906) . July 20, 1993 .
  • Fréjaville , C. , Karoui , H. , Tuccio , B. , Le Moigne , F. , Culcasi , M. , Pietri , S. , Lauricella , R. and Tordo , P. 1994 . J. Chem. Soc., Chem. Commun. , : 1793
  • Le Moigne , F. , Mercier , A. and Tordo , P. 1991 . Tetrahedron Lett. , 32 : 3841
  • Stipa , P. , Finet , J. P. , Le Moigne , F. and Tordo , P. 1993 . J. Org. Chem. , 58 : 4465
  • Dembkowski , L. , Finet , J. P. , Fréjaville , C. , Le Moigne , F. , Maurin , R. , Mercier , A. , Pages , P. , Stipa , P. and Tordo , P. 1993 . Free Rad. Res. Commun. , 19 : S23
  • Janzen , E. G. 1971 . Topics in Stereochemistry , Edited by: Allinger , N. L. and Eliel , E. L. Vol. 6 , 177 – 216 . New York : J. Wiley & Sons .
  • Rassat , A. and Rey , P. 1973 . Tetrahedron , 29 : 1599
  • Briere , R. , Lemaire , H. and Rassat , A. 1965 . Bull. Soc. Chim. Fr. , : 3273
  • Ricca , A. , Tronchet , J. M. J. , Weber , J. and Ellinger , Y. 1992 . J. Phys. Chem. , 96 : 10779
  • Rockenbauer , A. , Györ , M. , Hankouszky , H. O. and Hideg , K. 1988 . “ Electron Spin Resonance ” . In Specialist Periodical Report, Senior Reporter M.C.R. Symons Vol. 11A , 145 – 182 . Chap. 5
  • Janzen , E. G. and Liu , I-Ping . 1973 . J. Mag. Resonance , 9 : 513
  • Janzen , E. G. and Liu , I-Ping . 1973 . J. Mag. Resonance , 9 : 509
  • Vila , F. , Tordo , P. , Siri , D. and Pèpe , G. 1993 . Free Rad. Res. Comms. , 19 : S17 – S22 .
  • Fuchs , B. 1978 . Topics in Stereochemistry , Edited by: Allinger , N. L. and Eliel , E. L. Vol. 10 , 1 – 93 . New York : J. Wiley & Sons .
  • Lipnick , R. L. 1974 . J. Mol. Struct. , 21 : 411
  • Cremer , D. , Binkley , J. S. and Pople , J. A. 1976 . J. Am. Chem. Soc. , 98 : 6836
  • Anteunis , M. and Danneels , D. 1975 . Org. Magn. Resonance , 7 : 345
  • Gilchrist , J. , Duplan , J. C. and Infarnet , Y. 1988 . Chem. Phys. , 121 : 131
  • Pfafferott , G. , Oberhammer , H. , Boggs , J. E. and Caminati , W. 1985 . J. Am. Chem. Soc. , 107 : 2305
  • Lambert , J. B. , Papay , J. J. , Khan , S. A. , Kappauf , K. A. and Magyar , E. S. 1974 . J. Am. Chem. Soc. , 96 : 6112
  • Lambert , J. B. and Oliver , W. L. 1969 . J. Am. Chem. Soc. , 91 : 7774
  • Lambert , J. B. , Papay , J. J. , Magyar , E. S. and Neuberg , M. K. 1973 . J. Am. Chem. Soc. , 95 : 4458
  • Pitner , T. P. , Edwards , W. B. , Bassfield , R. L. and Whidby , J. F. 1978 . J. Am. Chem. Soc. , 100 : 246
  • Whidby , J. F. , Edwards , W. B. and Pitner , T. P. 1979 . J. Org. Chem. , 44 : 794
  • Pogliani , L. , Ellenberger , M. and Valat , J. 1975 . Org. Magn. Reson. , 7 : 61
  • Abraham , R. J. , Hudson , B. D. and Thomas , W. A. 1986 . Magn. Reson. Chem. , 24 : 812
  • Deber , C. M. , Torchia , D. A. and Blout , E. R. 1971 . J. Am. Chem. Soc. , 93 : 4893
  • Cycler , M. , Dobrynin , K. , Grabowski , M. J. , Nazarski , R. B. and Skowronski , R. 1985 . Chem. Soc. Perkin Trans. II , : 1495
  • Rabiller , C. , Denhel , A. and Lavielle , G. 1982 . Can. J. Chem. , 60 : 926
  • Infarnet , Y. , Duplan , J. C. and Huet , J. 1981 . J. Org. Magn. Reson. , 16 : 90
  • Schmitz , L. R. and Allinger , N. L. 1990 . J. Am. Chem. Soc. , 112 : 8307
  • Bukert , U. and Allinger , N. L. 1982 . Molecular Mechanics , Washington, D.C. : Marjorie C. Caserio, American Chemical Society .
  • Allinger , N. L. 1977 . J. Am. Chem. Soc. , 99 : 8127
  • Quantum Chemistry Program Exchange , U.S.A. : Indiana University . We used the Q.C.P.E. Program No. MM2 (87), furnished by the
  • Brutcher , F. V. Jr. , Roberts , T. , Barr , S. J. and Pearson , N. 1959 . J. Am. Chem. Soc. , 81 : 4915
  • Pèpe , G. and Genmol , D. Siri . 1990 . Modeling of Molecular Structure and Properties , Edited by: Rivail , J. L. 93 – 101 . Amsterdam : Elsevier Science .
  • The conformer populations have been calculated with Boltzmann distribution equation.
  • 47405 Bloomington, Indiana : Indiana University . LAOCN-5, QCPE-458, Chemistry Department;USA
  • Castellano , S. M. and Bothner-By , A. A. 1968 . Computer Program for Chemistry , Edited by: de Tar , D. F. Vol. 1 , 10 – 39 . New York : Benjamin .
  • Eloy , D. and Lauricella , R. Domino Program unpublished results.
  • Friedbolin , H. 1991 . Basic One and Two Dimensional NMR Spectroscopy , 89 – 91 . New York : VCH Publishers .
  • Bovey , A. F. 1970 . Nuclear Magnetic Resonance Spectroscopy , 362 – 363 . London : Academic Press .
  • Le Moigne , F. to be published.
  • Le Moigne , F. and Tordo , P. 1994 . J. Org. Chem. , 59 : 3365
  • The population and dihedral angles differences between envelope and twist conformations are small, then the weighted averages coupling constant values are very close to those corresponding to the lowest energy conformer.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.