Study of the mechanism of base induced dehydrobromination of trans-β-bromostyrene

Tetrahedron

Volumn 59, Issue 11, 2003, Pages 1995-2000

  Ma̧kosza, Mieczysław ^a   Chesnokov, Alexey A ^a  

^a POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

13C labeled compounds; Irreversible E1cB mechanism; trans bromostyrene; elimination

Indexed keywords

BASE; BETA BROMOSTYRENE; CATION; PROTON; STYRENE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; ELIMINATION REACTION; PH; PRIORITY JOURNAL;

EID: 0037430590     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00107-8     Document Type: Article

References (30)

1. Ma̧kosza M., Chesnokov A.A. Tetrahedron. 58:2002;7295-7301.
2. (a) Bordwell F.G. Acc. Chem. Res. 21:1988;456-463
3. (b) Bordwell F.G., Liu W.Z. J. Am. Chem. Soc. 118:1996;8777-8781.
4. (a) Smith M.B., March J. March's Advanced Organic Chemistry. 5th ed. 2001;Wiley, New York. pp 1331-1332
5. (b) Cope A.C. Org. React. 11:1960;317-493
6. (c) Cope A.C., LeBel N.A., Moore P.T., Moore W.R. J. Am. Chem. Soc. 83:1961;3861-3865.
7. Cristol S.J., Norris W.P. J. Am. Chem. Soc. 76:1954;3005-3009.
8. Schlosser M., Ladenberger V. Tetrahedron Lett. 1964;1945-1949.
9. Shimizu N., Shibata F., Tsuno Y. Bull. Chem. Soc. Jpn. 60:1987;777-778.
10. (a) Ohira S., Yamasaki K., Nozaki H., Yamato M., Nakayama M. Tetrahedron Lett. 36:1995;8843-8844
11. (b) Ohira S., Okai K., Moritani T. J. Chem. Soc. Chem. Commun. 1992;721-722
12. (c) Walsh R., Wolf C., Untiedt S., de Meijere A. J. Chem. Soc. Chem., Commun. 1992;421-422
13. (d) Colvin E.W., Hamill B.J. J. Chem. Soc., Perkin Trans. 1. 1977;869-874.
14. (a) Wolinsky J., Clark G.W., Thorstenson P.C. J. Org. Chem. 41:1976;745-750. and references cited therein
15. (b) Köbrich G., Ansari F. Chem. Ber. 100:1967;2011-2020
16. (c) Curtin D.Y., Crump J.W. J. Am. Chem. Soc. 80:1958;1922-1926.
17. (a) Smith M.B., March J. March's Advanced Organic Chemistry. 5th ed. 2001;Wiley, New York. pp 247-252
18. (b) Stevens I.D.R., Liu M.T.H., Soundararajan N., Paike N. Tetrahedron Lett. 30:1989;481-484
19. (c) Osamura Y., Schaeter H.F., Gray S.K., Miller W.H. J. Am. Chem. Soc. 103:1981;1904-1907.
20. Köbrich G. Angew. Chem., Int. Ed. Engl. 6:1967;41-52.
21. (a) Bothner-By A.A. J. Am. Chem. Soc. 77:1955;3293-3296
22. (b) Curtin D.Y., Flynn E.W., Nystron R.F. J. Am. Chem. Soc. 80:1958;4599-4601.
23. Cristol S.J., Helmreich R.F. J. Am. Chem. Soc. 77:1955;5034-5038.
24. Apeloig Y., Franke W., Rappoport Z., Schwarz H., Stahl D. J. Am. Chem. Soc. 103:1981;2770-2780.
25. 2O during decomposition of the bisulfite adduct of phenylacetaldehyde. Once isolated, the free aldehyde must be immediately used in the next stage.
26. Roman U., Knorr R., Behringer C., Ruhdorfer J. J. Prakt. Chem. 336:1994;260-262.
27. Ma̧kosza M., Chesnokov A.A. Tetrahedron. 56:2000;3553-3558.
28. 1.
29. Young R.N., Brocklehurst B., Booth P. J. Am. Chem. Soc. 116:1994;7885-7888.
30. Guijarro D., Guillena G., Mancheño B., Yus M. Tetrahedron. 50:1994;3427-3436.