The influence of ring size on the selectivity of phosphorus heterocycle aminolysis in the presence of water or alcohols - Case of 2-oxo- or 2-thioxo-3-sulfonyl-1,3,2-oxazaphosphorinanes

European Journal of Organic Chemistry

Volumn , Issue 8, 2006, Pages 1959-1964

  Dujols, Frédéric ^a   Mulliez, Michel ^a  

^a CNRS   (France)

Author keywords

Amino alcohols; Chemoselectivity; Phosphorus heterocycles; Phosphorylation; Sulfonamides

Indexed keywords

EID: 33646188014     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500743     Document Type: Article

References (18)

1. F. Dujols, L. Marty, M. Mulliez, Org. Biomol. Chem. 2005, 3, 227-232.
2. F. G. Bordwell, F. G. Algrim, J. Org. Chem. 1976, 41, 2507-2508.
3. G. Dauphin, A. Kergomard, Bull. Soc. Chim. France 1961, 486-492.
4. See inter alia: F. H. Westheimer, Acc. Chem. Res. 1968, 1, 70-78.
5. J. Emsley, D. Hall, The Chemistry of Phosphorus, Harper and Row, London, 1976, pp. 329-336.
6. P. Cazabonne, F. Dujols, M. Mulliez, Synthesis of Constrained N-Sufonylated Amino Alcohols, in preparation; F. Dujols' doctoral thesis [Université Paul Sabatier, Toulouse (France), 4-10-99], ch. VI.
7. No definite structure, such as chair or boat, could be determined.
8. M. Mulliez, Participation of Sulfonamides in the Reactions of Phosphorylation, in preparation; F. Dujols' doctoral thesis [Université Paul Sabatier, Toulouse (France), 4-10-99], ch. VII.
9. For acyclic compounds, see for example: V. E. Belskii, L. S. Novikova, L. A. Kudryatseva, B. E. Ivanov, Bull. Acad. Sci. USSR, Div. Chem. Sci., (Izv. Akad. Nauk SSSR, Ser. Khim Transl.) 1977, 1188-1202.
10. For cyclic compounds, see for example: M. Revel, J. Navech, F. Mathis, Bull. Soc. Chim. France 1971, 105-112.
11. See particularly: L. Horner, J. Prakt. Chem. 1992, 234, 645-6553 and references cited therein.
12. J. M. Grévy, M. Mulliez, J. Chem. Soc., Perkin Trans. 2 1995, 1809-1816.
13. M. Mulliez, Tetrahedron 1981, 37, 2027-2041.
14. F. Dujols, P. Jollet, M. Mulliez, Phosphorus Sulfur Silicon 1998, 134-135, 231-254.
15. G. Sosnovsky, M. Konieczny, Synthesis 1977, 618-619.
16. F. Dujols, M. Mulliez, Phosphorus Sulfur Silicon 2000, 157, 165-191.
17. More details are available in: F. Dujols' doctoral thesis: no. 3497, 1999, Université Paul Sabatier, Toulouse (France) .
18. F. Dujols, M. Mulliez, J. Heterocycl. Chem. 2001, 38, 475-480.