Carbon-bromine cleavage by dimethyl sulfoxide: the key step of C(5) functionalization of push-pull 2-alkylidene-4-oxothiazolidine vinyl bromides

Tetrahedron Letters

Volumn 48, Issue 10, 2007, Pages 1695-1698

  Baranac Stojanović, Marija ^a,b   Marković, Rade ^a,b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

C(5) Functionalization; Dimethyl sulfoxide; Push pull 2 alkylidene 4 oxothiazolidines; Vinyl bromides

Indexed keywords

ALKYL GROUP; BROMIDE; CARBON; DIMETHYL SULFOXIDE; THIAZOLIDINE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; BROMINATION; CHEMICAL BOND; CHEMICAL INTERACTION; ELIMINATION REACTION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 33846785296     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.051     Document Type: Article

References (37)

1. Epstein W.W., and Sweat F.W. Chem. Rev. 67 (1967) 247-260
2. Butterworth R.F., and Hanessian S. Synthesis (1971) 70-88
3. Mancuso A.J., and Swern D. Synthesis (1981) 165-185
4. Tidwell T.T. Synthesis (1990) 857-870
5. Dalton D.R., Hendrickson J.B., and Jones D. J. Chem. Soc., Chem. Commun. (1966) 591-592
6. Dalton D.R., Dutta V.P., and Jones D.C. J. Am. Chem. Soc. 90 (1968) 5498-5501
7. Hanessian S., Yang-Chung G., Lavallee P., and Pernet A.G. J. Am. Chem. Soc. 94 (1972) 8929-8931
8. Tatsugi J., and Izawa Y. J. Chem. Res. (S) (1988) 356-357
9. Uzagare M.C., Padiya K.J., Salunkhe M.M., and Sanghvi Y.S. Bioorg. Med. Chem. Lett. 13 (2003) 3537-3540
10. Dossena A., Marchelli R., and Casnati G. J. Chem. Soc., Perkin. Trans. 1 (1983) 1141-1144
11. Armani E., Dossena A., Marchelli R., and Casnati G. Tetrahedron 40 (1984) 2035-2039
12. Kallmayer H.-J., Burgardt S., and Doerr M. Scientia Pharmaceutica 64 (1996) 25-30
13. Nakajima N., Saito M., and Ubukata M. Tetrahedron 58 (2002) 3561-3577
14. Khenkin A.M., and Neumann R. J. Am. Chem. Soc. 124 (2002) 4198-4199
15. Iwanami K., Hinakubo Y., and Oriyama T. Tetrahedron Lett. 46 (2005) 5881-5883
16. Taksande K.N., Sakate S.S., and Lokhande P.D. Tetrahedron Lett. 47 (2006) 643-646
17. Yin G., Zhou B., Meng X., Wu A., and Pan Y. Org. Lett. 8 (2006) 2245-2248
18. Nace H.R., and Monagle J.J. J. Org. Chem. 24 (1959) 1792-1793
19. Albright J.D., and Goldman L. J. Am. Chem. Soc. 89 (1967) 2416-2423
20. Mancuso A.J., Huang S.-L., and Swern D. J. Org. Chem. 43 (1978) 2480-2482
21. Albright J.D. J. Org. Chem. 39 (1974) 1977-1979
22. All vinyl bromides were obtained by bromination of the parent 2-alkylidene-4-oxothiazolidines using molecular bromine.
23. Kuwajima I., and Nakamura E. In: Trost B.M., Fleming I., and Heathcock C.H. (Eds). Comprehensive Organic Synthesis Vol. II (1991), Pergamon, Oxford 441-473
24. Negishi E. J. Organomet. Chem. 576 (1999) 179-194
25. 3S: C, 40.14; H, 2.76; N, 8.51; S, 9.74. Found: C, 40.22; H, 2.76; N, 8.44; S, 9.47.
26. Marković R., Baranac M., and Džambaski Z. Heterocycles 63 (2004) 851-860
27. Sandström J. Top. Stereochem. 14 (1983) 83-181
28. There is also a steric effect, due to the bulk of an acceptor substituent, which facilitates the C-Br bond cleavage-unpublished data.
29. Johnson A.P., and Pelter A. J. Chem. Soc. (1964) 520-522
30. Pfitzner K.E., and Moffatt J.G. J. Am. Chem. Soc. 87 (1965) 5661-5670
31. De Luca L., Giacomelli G., and Porcheddu A. J. Org. Chem. 66 (2001) 7907-7909
32. Alternatively, direct hydrolysis 11→2 may occur in the presence of water, preceding the formation of 12.
33. Aida T., Akasaka T., Furukawa N., and Oae S. Bull. Chem. Soc. Jpn. 49 (1976) 1117-1121
34. Aida T., Furukawa N., and Oae S. Tetrahedron Lett. (1973) 3853-3856
35. Since DMSO was a solvent in these reactions and was not dried prior to use, it contained the necessary amount of water for the beginning of the reaction.
36. Marković R., and Baranac M. Synlett (2000) 607-610
37. Marković R., Džambaski Z., and Baranac M. Tetrahedron 57 (2001) 5833-5841