Sulfonyl bis-N-oxazolidinone (SBO): A new versatile dielectrophile with sequential reactivity

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8691-8694

  Dewynter, Georges ^a,c   Abdaoui, Mohamed ^a,d   Toupet, Loic ^b   Montero, Jean Louis ^a  

^a UNIV MONTPELLIER   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITÉ LAVAL   (Canada)

^d UNIVERSITY OF GUELMA   (Algeria)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE; SULFAMIDE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE; X RAY CRYSTALLOGRAPHY;

EID: 0030778179     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10336-7     Document Type: Article

References (16)

1. Dewynter, G.; Abdaoui, M.; Regainia, Z.; Montero, J-L. Tetrahedron, 1996, 52, 14217-14224.
2. Abdaoui, M.; Dewynter, G.; Montero, J-L. Tetrahedron Lett., 1996, 37, 5695-5698.
3. Encyclopedia of Reagents for Organic Synthesis. dir. by L. Paquette. John Wiley and sons Edt. Chichester (UK). 1995. BOP-Cl: vol 1, p.543. CDI: vol 2, p. 1006. sulfuryl diimidazole vol 7., p.4709.
4. Encyclopedia of Reagents for Organic Synthesis. dir. by L. Paquette. John Wiley and sons Edt. Chichester (UK). 1995. BOP-Cl: vol 1, p.543. CDI: vol 2, p. 1006. sulfuryl diimidazole vol 7., p.4709.
5. Encyclopedia of Reagents for Organic Synthesis. dir. by L. Paquette. John Wiley and sons Edt. Chichester (UK). 1995. BOP-Cl: vol 1, p.543. CDI: vol 2, p. 1006. sulfuryl diimidazole vol 7., p.4709.
6. Encyclopedia of Reagents for Organic Synthesis. dir. by L. Paquette. John Wiley and sons Edt. Chichester (UK). 1995. BOP-Cl: vol 1, p.543. CDI: vol 2, p. 1006. sulfuryl diimidazole vol 7., p.4709.
7. Appel, R.; Senkpiel, W. Angew. Chem. 1958, 70, 271297. and Chem. Ber. 1958, 91, 1200.
8. Appel, R.; Senkpiel, W. Angew. Chem. 1958, 70, 271297. and Chem. Ber. 1958, 91, 1200.
9. 3a 1.1585 0.3373 0.2317 5* H3b 1.0707 0.1259 0.3002 5* Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3) * [a2*B(1,1) + b2*B(2,2) + c2*B(3,3) + ab(cos y)*B(1,2)+ ac(cos ß)*B(1,3) + bc(cos α)*B(2,3)] H atoms refined isotropically.
10. 3a 1.1585 0.3373 0.2317 5* H3b 1.0707 0.1259 0.3002 5* Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3) * [a2*B(1,1) + b2*B(2,2) + c2*B(3,3) + ab(cos y)*B(1,2)+ ac(cos ß)*B(1,3) + bc(cos α)*B(2,3)] H atoms refined isotropically.
11. 3a 1.1585 0.3373 0.2317 5* H3b 1.0707 0.1259 0.3002 5* Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3) * [a2*B(1,1) + b2*B(2,2) + c2*B(3,3) + ab(cos y)*B(1,2)+ ac(cos ß)*B(1,3) + bc(cos α)*B(2,3)] H atoms refined isotropically.
12. 3a 1.1585 0.3373 0.2317 5* H3b 1.0707 0.1259 0.3002 5* Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3) * [a2*B(1,1) + b2*B(2,2) + c2*B(3,3) + ab(cos y)*B(1,2)+ ac(cos ß)*B(1,3) + bc(cos α)*B(2,3)] H atoms refined isotropically.
13. Bonnaud, B.; Agoh, B.; Delaunay, B.; Dewynter, G.; Montero J-L.; Aycard, J-P. Acta Cryst., 1987, C-43, 2466-2468.
14. In this case, SBO reacts as catecholsulfate (see ref 3, vol 2, p. 1020). Dibenzylsulfamide 3 is identified by NMR. mp: 181° C (Lit. 180-182° C, Helferich, B.; Wiehle, D. J. Prakt. Chem. 1961, 14, 177.
15. 2 Pr+pip), 0.9 (t, 3H, CH3 Pr).
16. Nakanishi, K.; Salomon, P.H.; Infrared Absorption Spectroscopy, Holden-Day. San Francisco. 1977.