Studies on electrophilic reaction of Br2 with 1,2-allenylic sulfones. A highly regio- and stereoselective synthesis of 1-phenylsulfonyl-2-bromo-1(E)-alken-3-ols and 1-phenylsulfonyl-2-bromo-1(E),3(E)-butadienes

Tetrahedron

Volumn 63, Issue 32, 2007, Pages 7612-7616

  Zhou, Chao ^a   Fu, Chunling ^a   Ma, Shengming ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,2 Allenylic sulfones; Bromine; Bromohydroxylation; Mechanistic study

Indexed keywords

ALKENE DERIVATIVE; ALLENE DERIVATIVE; BROMINE; BUTANE; SULFONE DERIVATIVE;

ARTICLE; BROMINATION; ELIMINATION REACTION; HYDROXYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 34250751710     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.05.039     Document Type: Article

References (26)

1. For most recent reviews on the chemistry of allenes, see:
2. Krause N., and Hashmi A.S.K. Modern Allene Chemistry (2004), Wiley-VCH, Weinheim
3. Ma S. Chem. Rev. 105 (2005) 2829
4. For a review on electrophilic addition of allenes, see: Ma, S. Chapter 10 in Ref. 1a.
5. Katrizky A.R., and Feng D. J. Org. Chem. 62 (1997) 715
6. Kocienski P., and Whitby R. Synthesis (1991) 1029
7. Hiof H., and Natsuas K. Liebigs Ann. Chem. (1988) 705
8. Mueller W.H., and Butler P.E. J. Org. Chem. 33 (1968) 1533
9. Ma S., and Wu S. J. Org. Chem. 64 (1999) 9314
10. Ma S., and Wu S. Tetrahedron Lett. 42 (2001) 4075
11. Fu C., and Ma S. Eur. J. Org. Chem. 18 (2005) 3942
12. Ma S., Wei Q., and Wang H. Org. Lett. 2 (2000) 3893
13. Ma S., Ren H., and Wei Q. J. Am. Chem. Soc. 125 (2003) 4817 and the references cited therein
14. Ma S., Hao X., and Huang X. Org. Lett. 5 (2003) 1217
15. Ma S., Hao X., Meng X., and Huang X. J. Org. Chem. 69 (2004) 5720
16. Ma S., Hao X., and Huang X. Chem. Commun. (2003) 1082
17. 2 with 1,2-propadienyl phenyl sulfone, see:
18. Padwa A., Murphree S., and Yeske P. J. Org. Chem. 55 (1990) 4241
19. Padwa A., and Ishida M. Tetrahedron Lett. 32 (1991) 5673
20. 2 with bisallenic sulfones forming γ-sultines, see:
21. Braverman S., and Duar Y. J. Am. Chem. Soc. 105 (1983) 1061
22. Braverman S., and Reisman D. J. Am. Chem. Soc. 99 (1977) 605
23. int=0.063) number of observations 2896 [I>2σ(I)], parameter 342, CCDC 614239.
24. int=0.1978) number of observations 2152 [I>2σ(I)], parameter 164, CCDC 614241.
25. Cadogan J.I.G., Cameron D.K., Gosney I., Millar J.R.A., Newlands S.F., and Reed D. J. Chem. Soc., Perkin Trans. 2 (1996) 2309
26. Cossu S., de Lucchi O., and Dilillo F. Gazz. Chim. Ital. 121 (1991) 533