Expeditious synthesis of β-cycloacetalic sulfoxides. Introducing 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE), a promising new alkenylsulfur reagent

Tetrahedron Letters

Volumn 46, Issue 6, 2005, Pages 1035-1037

  Cabianca, Elena ^a   Tatibouët, Arnaud ^a   Fabris, Fabrizio ^b   De Lucchi, Ottorino ^b   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

Carbohydrates; Cyclic acetals; Protecting groups; Sulfoxides

Indexed keywords

1 PHENYLSULFINYL 2 PHENYLSULFANYLETHYLENE; ALCOHOL DERIVATIVE; BIS(1,2 PHENYLSULFONYL)ETHYLENE; CARBOHYDRATE; ETHYLENE DERIVATIVE; REAGENT; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; PHYSICAL CHEMISTRY; REACTION ANALYSIS;

EID: 12344299389     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.151     Document Type: Article

References (14)

1. O. De Lucchi, and L. Pasquato L.A. Paquette Enyclopedia of Reagents for Organic Synthesis Vol. 1 1995 Wiley & Sons New York 547 549 and First Update by Rollin, P., Tatibouët, A., in press
2. E. Cabianca, F. Chéry, P. Rollin, O. De Lucchi, and S. Cossu Synlett 2001 1962 1964
3. F. Chéry, M. Desroses, A. Tatibouët, P. Rollin, and O. De Lucchi Tetrahedron 59 2003 4563 4572
4. E. Cabianca, F. Chéry, P. Rollin, A. Tatibouët, and O. De Lucchi Tetrahedron Lett. 43 2002 585 587
5. F. Chéry, P. Rollin, O. De Lucchi, and S. Cossu Synthesis 2 2001 286 292
6. Cabianca, E.; Chéry, F.; Rollin, P.; Tatibouët, A.; De Lucchi, O., unpublished results
7. N.W. Cusa, and H. McCombie J. Chem. Soc. 1937 767 770
8. W.E. Truce, M.M. Boudakian, R.F. Heine, and R.J. McManimie J. Am. Chem. Soc. 78 1956 2743 2748
9. Aryl monosulfoxides of the SOSE-type were once mentioned as side-products by Montanari & coll., see G. Farina, F. Montanari, and A. Negrini Gazz. Chim. Ital. 89 1959 1548 1563
10. 2: calcd 260.0330; found 260.0343
11. 4, concentrated under reduced pressure and the crude product was purified by silica gel column chromatography
12. 6S: calcd 340.0981; found 340.0969
13. 2: calcd 260.0330; found 260.0346
14. See for example: O. De Lucchi, U. Miotti, and G. Modena Org. React. 40 1991 157 405