142
Views
1
CrossRef citations to date
0
Altmetric
Original Articles

Facile Phosphite to Phosphonate Rearrangement of a Trialkanolamine-derived Triphosphite Promoted by TriethylaluminumCitation1

, , , , &
Pages 2611-2623 | Received 07 Nov 2006, Accepted 04 May 2007, Published online: 25 Sep 2007

REFERENCES AND NOTES

  • 1995 . Presented in part at the 17th International Conf. on Adv. in Stabilization and Degradation of Polymers . June 12–14 1995 , Luzern , Switzerland.
  • RajanBabu , T. V. and Casalnuovo , A. L. 1992 . J. Am. Chem. Soc. , 114 : 6265
  • Bendayan , A. , Masotti , H. , Peiffer , G. , Siv , C. and Archavlis , A. J. 1993 . Organomet. Chem. , 444 : 41
  • Casalnuovo , A. L. , RajanBabu , T. V. , Ayers , T. A. and Warren , T. H. 1994 . J. Am. Chem. Soc. , 116 : 9869
  • Higashizima , T. , Sakai , N. , Nozaki , K. and Takaya , H. 1994 . Tetrahedron Lett. , 35 : 2023
  • Sakai , N. , Nozaki , K. , Mashima , K. and Takaya , H. 1994 . Tetrahedron Asymmetry , 3 : 583
  • Cuny , G. D. and Buchwald , S. L. 1993 . J. Am. Chem. Soc. , 115 : 2066
  • Moasser , B. , Gross , C. and Gladfelther , W. L. 1994 . J. Organomet. Chem. , 471 : 201
  • Moasser , B. and Gladfelther , W. L. 1995 . Organometallics , 14 : 3832
  • Billig , E. , Abatjoglou , A. G. and Bryant , D. R. U.S. Patent 4,748,261 . 1988 . Chem. Abstr. 107, 7392 (1987)
  • Babin , J. E. and Whiteker , G. T. U.S. Patent 5,360, 938 . 1994 . Chem. Abstr. 122, 186609 (1995)
  • Buisman , G. J. H. , Kamer , P. C. J. and van Leeuwen , P. W. N. M. 1993 . Tetrahedron: Asymmetry , 4 : 1625
  • van Leeuwen , P. W. N. M. , Buisman , G. J. H. , van Rooy , A. and Kamer , P. C. J. 1994 . Recl. Trav. Chim. Pays-Bas. , 113 : 61
  • Jongsma , T. , Fossen , M. , Challa , G. and van Leeuwen , P. W. N. M. 1993 . J. Molecular Cat. , 83 : 17
  • van Rooy , A. , Orij , E. N. A. , Kamer , P. C. J. and van Leeuwen , P. W. N. M. 1995 . Organometallics , 14 : 34
  • Buisman , G. J. H. , Martin , M. E. , Vos , E. J. , Klootwijk , A. , Kamer , P. C. J. and van Leeuwen , P. W. N. M. 1995 . Tetrahedron: Asymmetry , 6 : 719
  • Buisman , G. J. H. , van der Veen , L. A. , Klootwijk , A. , de Lange , W. G. J. , Kamer , P. C. J. , van Leeuwen , P. W. N. M. and Vogt , D. 1997 . Organometallics , 16 : 2929
  • van der Veen , L. A. , Keeven , P. H. , Shoemaker , G. C. , Reek , J. N. H. , Kamer , P. C. J. , van Leeuwen , P. W. N. M. , Lutz , M. and Spek , A. L. 2000 . Organometallics , 19 : 872
  • Baker , M. J. , Harrison , K. N. , Orpen , A. G. , Pringle , P. G. and Shaw , G. 1991 . J. Chem. Soc., Chem. Commun. , : 803
  • Bedford , R. B. , Chaloner Castillòn , P. A. , Claver , C. , Fernandez , E. , Hitchcock , R. B. and Ruiz , A. 1996 . Organometallics , 15 : 3990
  • Kadyrov , R. , Heller , D. and Selke , R. 1998 . Tetrahedron: Asymmetry , 9 : 329
  • Cserépi-Szúcs , S. , Tóth , I. , Párkányi , L. and Bakos , J. 1998 . Tetrahedron: Asymmetry , 9 : 3135
  • Diéguez , M. , Ruiz , A. and Claver . 2002 . J. Org. Chem. , 67 : 3796 and references therein
  • Pastor , S. D. , Rogers , J. S. , Ali NabiRahni , M. and Stevens , E. D. 1996 . Inorg. Chem. , 35 : 2157
  • Pastor , S. D. , Shum , S. P. , DeBellis , A. D. , Burke , L. P. , Rodebaugh , R. K. , Clarke , F. H. and Rihs , G. 1996 . Inorg. Chem. , 35 : 949
  • Smith , A. R. , Bruno , J. W. and Pastor , S. D. 2002 . Phosphorus, Sulfur, Silicon Relat. Elem. , 177 : 479
  • Pastor , S. D. and Shum , S. P. 1998 . Tetrahedron: Asymmetry , 9 : 543
  • Shum , S. P. , Pastor , S. D. , DeBellis , A. D. , Odorisio , P. A. , Burke , L. , Clark , F. H. , Rihs , G. , Piatek , B. and Rodebaugh , R. K. 2003 . Inorg. Chem. , 42 : 5097
  • Karsch , H. H. , Appelt , A. , Köhler , F. and Müller , G. 1985 . Organometallics , 4 : 231 For an example of a molecule with phosphorus coordinated to aluminum, see
  • Robinson , G. H. 1993 . Coordination Chemistry of Aluminum , New York : VCH . For a review, see, Chapter 1
  • Verkade , J. G. and Mosbo , J. A. 1987 . Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis: Organic Compounds and Metal Complexes , Edited by: Quin , L. D. and Verkade , J. G. 446 Weinheim : VCH .
  • James , D. 1986 . Encyclopedia of Polymer Science and Engineering , Vol 6 , 454 New York : Wiley-Interscience . For reviews and leading references, see
  • Lieberman , R. B. 1986 . Encyclopedia of Polymer Science and Engineering , Vol 13 , 429 New York : Wiley-Interscience .
  • Gugumus , F. 1990 . Plastics Additives, , 3rd ed. , New York : Hanser . Chapter 1
  • Horton , A. D. 1994 . Trends in Poly. Sci. , 2 : 158 For a review, see
  • Parshall , G. W. and Ittel , S. D. 1992 . Homogeneous Catalysis, , 2nd ed. , New York : Wiley-Interscience . For examples of catalyst systems incorporating trialkylaluminum co-catalysts, see
  • Spivack , J. D. , Pastor , S. D. , Patel , A. and Steinhuebel , L. P. 1985 . Polymer Stabilization and Degradation: ACS Symposium Series 280 , Edited by: Klemchuk , P. P. 247 – 257 . Washington , D.C. : American Chemical Society .
  • Sander , M. 1961 . Angew. Chem. , 73 : 67
  • Shum , S. P. , Pastor , S. D. and Rihs , G. 2002 . Inorg. Chem. , 41 : 127
  • Odorisio , P. A. , Pastor , S. D. and Spivack , J. D. 1984 . Phosphorus Sulfur , 19 : 1
  • Odorisio , P. A. , Pastor , S. , Spivack , D. J. D. , Bini , D. and Rodebaugh , R. K. 1984 . Phosphorus Sulfur , 19 : 285
  • Pastor , S. D. , Shum , S. P. , Rodebaugh , R. K. , DeBellis , A. D. and Clarke , F. H. 1993 . Helv. Chim. Acta , 76 : 900 For the isolation and characterization of 4, see
  • Eliel , E. L. , Wilen , S. H. and Mander , L. N. 1994 . Stereochemistry of Organic Compounds , 54 – 58 . New York : Wiley-Interscience . For a discussion of averaged symmetry, residual stereoisomers, and the NMR of conformationally mobile systems, see
  • DeBellis , A. D. Calculations were performed using MacroModel version 7.0 and Spartan version 5.1 on an SGI Octane or DEC Alphaserver 4000 workstation private communication
  • Nykerk , K. M. 1968 . Inorg. Nucl. Chem. Lett. , 4 : 253
  • Hendrickson , C. H. , Duffy , D. and Eyman , D. P. 1968 . Inorg. Chem. , 7 : 1047 The dissociation enthalpy of an adduct of AlMe3 with trimethylphosphine oxide is 32 kcal·mole-1, see
  • The 31P1H NMR spectra of the reaction media showed clean conversion of 1 to 5, with no other phosphorus containing species. The slight chemical shift difference observed for 5 in the crude reaction mixture suggests that the product was complexed to Al, which is consistent with the observations by Sander (Ref. 17). The Al that was complexed to 5 in the crude reaction mixture was removed by hydrolysis during chromatographic purification. Unfortunately, the ultimate fate of the Al could not be determined and we suggest it remains on the column after chromatographic purification of the crude reaction mixture. Considerable loss of product on the column accounts for the low isolated yields, which has been observed previously for high-molecular-phosphites of this structural class that contain aminic nitrogen
  • Odorisio , P. A. , Pastor , S. D. and Spivack , J. D. 1984 . Phosphorus Sulfur , 20 : 273 For 1H NMR spectral data of a phosphonate derivative incorporated in a dibenzo[d,f][1,3,2]dioxaphosphepin ring, see
  • Nakanishi , K. , ed. 1990 . One-dimensional and Two-dimensional NMR Spectra by Modern Pulse Techniques , Sausalito : University Science Books . For an overview of the technique and application examples, see
  • Quin , L. D. 2000 . A Guide to Organophosphorus Chemistry , 141 – 145 . New York : Wiley-Interscience . For a recent review of the Michaelis-Arbusov reaction, see
  • Emsley , J. and Hall , D. 1976 . The Chemistry of Phosphorus , 117 – 119 . London : Harper and Row . For earlier reviews, see
  • Hudson , R. F. 1965 . Structure and Mechanism in Organo-phosphorus Chemistry , 135 – 140 . New York : Academic Press .
  • Harvey , R. G. and De Sombre , E. R. 1964 . Topics in Phosphorus Chemistry , 1 : 57
  • Kosolapoff , G. M. 1950 . Organophosphorus Compounds , 196 – 199 . New York : Wiley .
  • Arbusov , B. A. 1964 . Organo-Phosphorus Compounds , 307 – 335 . London : Butterworths .
  • Arbuzov , B. A. and Grechnik , N. P. 1947 . Zhur. Obshcheĭ Khim , 17 : 2166
  • Arbuzov , B. A. and Pudovik , A. N. 1947 . Zhur. Obshcheĭ Khim. , 17 : 2158
  • Saunders , S. and Wild , W. 1948 . J. Chem. Soc. , : 699
  • Edmundson , R. S. 1996 . The Chemistry of Organophosphorus Compounds , Edited by: Hartley , F. R. Vol. 4 , 62 – 69 . Chichester : Wiley . For a review of variations of the Michaelis-Arbusov reaction, see
  • 2001 . Pure Appl. Chem. , 73 : 1795 See IUPAC recommendation on reporting 15N chemical shift values
  • Stabilization as a result of chelation of Al to the phosphonate oxygen

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.