Molecular rearrangement in the Birch reduction of dibenzothiophenes

Tetrahedron Letters

Volumn 48, Issue 32, 2007, Pages 5657-5659

  Kukula, Pavel ^a   Dutly, Andreas ^a   Rüegger, Heinz ^a   Prins, Roel ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Birch reduction; Dibenzothiophene; Hydrodesulfurization (HDS); Rearrangement; Ring closure; Ring opening; Sulphur containing heterocycles

Indexed keywords

4,6 DIMETHYLDIBENZOTHIOPHENE; DIBENZOTHIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIRCH REDUCTION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 34447263507     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.026     Document Type: Article

References (24)

1. Birch A.J., and Smith H. Rev. Chem. Soc. 4 (1950) 69
2. Birch A.J. Pure Appl. Chem. 68 (1996) 553
3. Donohoe T.J., Garg R., and Stevenson C.A. Tetrahedron: Asymmetry 7 (1996) 317
4. Donohoe T.J., Raoof A., Linney I.D., and Helliwell M. Org. Lett. 3 (2001) 861
5. Donohoe T.J., Mace L., Helliwell M., and Ichihara O. Synlett (2002) 331
6. Paul T., Malachowski W.P., and Lee J. J. Org. Chem. 72 (2007) 930
7. Birch A.J., and Slobbe J. Heterocycles 5 (1976) 905
8. Rabideau P.W., and Marcinow Z. Org. React. 42 (1992) 1-334
9. Donohoe T.J., Guyo P.M., and Raoof A. Targets in Heterocyclic Systems 3 (1999) 117
10. Kukula P., Gramlich V., and Prins R. Helv. Chim. Acta 89 (2006) 1623
11. Gilman H., and Jacoby A.L. J. Org. Chem. 3 (1938) 108
12. Hückel W., and Nabih I. Chem. Ber. 89 (1956) 2115
13. Francisco M.A., Kurs A., Katritzky A.R., and Rasala D. J. Org. Chem. 53 (1988) 596
14. Birch A.J., and Nasipuri D. Tetrahedron 6 (1959) 148
15. Hückel W., Gupté S., and Wartini M. Chem. Ber. 99 (1966) 1388
16. Birch A.J. J. Chem. Soc. (1944) 430
17. Birch A.J., Hinde A.L., and Radom L. J. Am. Chem. Soc. 102 (1980) 3370
18. Zimmerman H.E., and Wang P.A. J. Am. Chem. Soc. 115 (1993) 2205
19. Oku A., Tsuji H., Yoshida M., and Yoshiura N. J. Am. Chem. Soc. 103 (1981) 1244
20. Oku A., Yoshiura N., and Okuda T. J. Org. Chem. 48 (1983) 619
21. Bethell D., McDowall L.J., and Parker V.D. J. Chem. Soc., Chem. Commun. (1984) 308
22. Friedman M., Cavins J.F., and Wall J.S. J. Am. Chem. Soc. 87 (1985) 3672
23. Bernasconi C.F., and Killion R.B. J. Am. Chem. Soc. 110 (1988) 7506
24. Miyata O., Shinada T., Ninomiya I., Naito T., Date T., Okamura K., and Inagaki S. J. Org. Chem. 56 (1991) 6556