Anchimeric assistance of the sulfinyl group in the hydrolysis of cyano groups: A new mild method for the reduction of sulfoxides

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4569-4572

  García Ruano, Jose L ^a   Martín Castro, Ana M ^a   Rodriguez Ramos, Jesús H ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; ORGANIC CHEMISTRY; REACTION TIME; REDUCTION; SYNTHESIS;

EID: 0030600167     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00848-9     Document Type: Article

References (19)

1. 1. García Ruano, J.L.; Martín Castro, A.M.; Rodriguez, J.H. Tetrahedron Lett. 1991, 32, 3195.
2. 2. García Ruano, J.L.; Martín Castro, A.M.; Rodríguez, J.H. J. Org. Chem. 1992, 57, 7235.
3. 3. García Ruano, J.L.; Martín Castro, A.M.; Rodríguez, J.H. J. Org. Chem. 1994, 59, 533.
4. 4. Sarel, S.; Newman, M.S. J. Am. Chem. Soc. 1956, 78, 5416. Tsai, L.; Miwa, T.; Newman, M.S. J. Am. Chem. Soc. 1957, 79, 2530. Becke, F.; Fleig, H.; Pässler, P. Liebigs Ann. Chem. 1971, 749, 198. Houser, C.R., Hoffenberg, D.S. J Org. Chem. 1955, 20, 1448. Hauser, C.P.; Eby, C.J. J. Am. Chem. Soc. 1957, 79, 725.
5. 4. Sarel, S.; Newman, M.S. J. Am. Chem. Soc. 1956, 78, 5416. Tsai, L.; Miwa, T.; Newman, M.S. J. Am. Chem. Soc. 1957, 79, 2530. Becke, F.; Fleig, H.; Pässler, P. Liebigs Ann. Chem. 1971, 749, 198. Houser, C.R., Hoffenberg, D.S. J Org. Chem. 1955, 20, 1448. Hauser, C.P.; Eby, C.J. J. Am. Chem. Soc. 1957, 79, 725.
6. 4. Sarel, S.; Newman, M.S. J. Am. Chem. Soc. 1956, 78, 5416. Tsai, L.; Miwa, T.; Newman, M.S. J. Am. Chem. Soc. 1957, 79, 2530. Becke, F.; Fleig, H.; Pässler, P. Liebigs Ann. Chem. 1971, 749, 198. Houser, C.R., Hoffenberg, D.S. J Org. Chem. 1955, 20, 1448. Hauser, C.P.; Eby, C.J. J. Am. Chem. Soc. 1957, 79, 725.
7. 4. Sarel, S.; Newman, M.S. J. Am. Chem. Soc. 1956, 78, 5416. Tsai, L.; Miwa, T.; Newman, M.S. J. Am. Chem. Soc. 1957, 79, 2530. Becke, F.; Fleig, H.; Pässler, P. Liebigs Ann. Chem. 1971, 749, 198. Houser, C.R., Hoffenberg, D.S. J Org. Chem. 1955, 20, 1448. Hauser, C.P.; Eby, C.J. J. Am. Chem. Soc. 1957, 79, 725.
8. 4. Sarel, S.; Newman, M.S. J. Am. Chem. Soc. 1956, 78, 5416. Tsai, L.; Miwa, T.; Newman, M.S. J. Am. Chem. Soc. 1957, 79, 2530. Becke, F.; Fleig, H.; Pässler, P. Liebigs Ann. Chem. 1971, 749, 198. Houser, C.R., Hoffenberg, D.S. J Org. Chem. 1955, 20, 1448. Hauser, C.P.; Eby, C.J. J. Am. Chem. Soc. 1957, 79, 725.
9. 5. The experimental procedure and physical and spectroscopical data of compounds 1 and 2 are described in refs. 1-3.
10. 6. Herranz, R; Castro-Pichel, J.; Vinuesa, S.; García López, M.T. J. Org. Chem. 1990, 55, 2232.
11. 7. In these reactions, 1f-1j are used as mixtures of diastereomers (epimers at C-α) and, consequently, 2f-2j are also obtained as mixtures of isomers in the same ratio than that of the corresponding starting products.
12. 8. A small proportion of one sulfinyl carboxamide (which disappeared with the time) was also isolated under these conditions. As this compound has been also isolated under other hydrolysis conditions, we are currently elucidating its structure, optimizing the conditions required for its formation and investigating both the mechanism and the synthetic scope of this reaction.
13. 9. Hayes, R.A. ; Martin, J.C. Sulfurane Chemistry, in Organic Sulfur Chemistry, Bernardi, F. ; Csizmadia, I.G. ; Mangini, A., Eds. Elsevier, Amsterdan, 1985, 408.
14. N2 process at the sulfur atom, with concomitant formation of the CI-S bond and breaking of the S-O bond, yielding the chlorosulfonium carboxamide. The evolution of this species would be similar to that proposed for the sulfurane C in Scheme 2.
15. 2=H) in diethyl ether, previously saturated with hydrogen chloride, under argon, was connected to a solution of sodium iodide in diethyl ether. As the chlorine evolved, the characteristic colour of iodine in the solution could be clearly detected.
16. 2AlCN.
17. 2)], in both spectra.
18. 2, washed with brine, and concentrated.
19. 15. Vankar, Y.D.; Trinidha Rao, C. Tetrahedron Lett. 1985, 26, 2717.