A kinetic, product and kinetic isotope effect investigation of the bromination of 1,1-diphenylethyIenes and of their 2,2-dideuterio derivatives

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 1997, Pages 581-584

  Bellucci, Giuseppe ^a   Chiappe, Cinzia ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347832973     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605390d     Document Type: Article

References (27)

1. (a) G. H. Schmid and D. G. Garrat, The Chemistry of Double-Bonded Functional Groups, ed. S. Patai, Wiley, New York, 1977; Suppl. A, Part 2, p. 725;
2. (b) P. B. D. De la Mare and R. Bolton, Electrophilic Additions to Unsaturated Systems, Elsevier, New York, 2nd edn., 1982, p. 136;
3. K. A. V'yunov and A. Guniak, I., Russ Chem. Rev. (Engl. Trans.), 1981, 50, 151.
4. For recent reviews see: (a) G. H. Schmid, The Chemistry of Double-Bonded Functional Groups, ed. S. Patai, Wiley, New York, 1989; suppl. A, vol. 2 pt. 1. p. 699;
5. (b) M. F. Ruasse, Adv. Phys Org. Chem., 1993, 28, 207.
6. (a) R. S. Brown, R. Gedye, H. Slebocka-Tilk, J. M. Buschek and K. R. Kopecky, J. Am. Chem. Soc., 1984, 106, 4515;
7. (b) G. Bellucci, C. Chiappe and F. Marioni, J. Am. Chem. Soc., 1987, 109, 515;
8. (c) G. Bellucci, R. Bianchini, C. Chiappe, F. Marioni and R. Spagna, J. Am. Chem. Soc., 1988, 110, 546;
9. (d) M. F. Ruasse, S. Motallebi and B. Galland, J. Am. Chem. Soc., 1991, 113, 3440;
10. (e) G. Bellucci, C. Chiappe, F. Marioni and F. Marchetti, J. Phys. Org. Chem., 1991, 4, 387;
11. (f) G. Bellucci, R. Bianchini, C. Chiappe, R. S. Brown and H. Slebocka-Tilk, J. Am. Chem. Soc., 1991, 113, 8012;
12. (g) G. Bellucci, R. Bianchini, C. Chiappe, R. Ambrosetti, D. Catalano, A. J. Bennet, H. Slebocka-Tilk, M. G. H. Aarts and R. S. Brown, J. Org. Chem., 1993, 58, 3401;
13. (h) C. Y. Zheng, H. Slebocka-Tilk, R. W. Nagorski, L. Alvarado and R. S. Brown, J. Org. Chem., 1993, 58, 2122;
14. (i) R. W. Nagorski, H. Slebocka-Tilk and R. S. Brown, J. Am Chem. Soc., 1994, 116, 419.
15. G. Bellucci, C. Chiappe, R. Bianchini, D. Lenoir and R. Merges, J. Am. Chem. Soc., 1995, 117, 12001.
16. R. Nagorski and R. S. Brown, J. Am. Chem. Soc., 1992, 114, 7773.
17. M. F. Ruasse, Acc. Chem. Res., 1990, 23, 87.
18. (a) R. S. Brown, H. Slebocka-Tilk, A. J. Bennet, G. Bellucci, R. Bianchini and R. Ambrosettil J. Am. Chem. Soc., 1990, 112, 6310;
19. (b) H. Slebocka-Tilk, C. Y. Zheng and R. S. Brown, J. Am. Chem. Soc., 1993, 115, 1347;
20. (c) G. Bellucci, R. Bianchini, C. Chiappe, D. Lenoir and A. Attar, J. Am. Chem. Soc., 1995, 117, 6243.
21. L. F. Fieser, J. Chem. Educ., 1954, 31, 291.
22. R. Bianchini and C. Chiappe, J. Org. Chem., 1992, 57, 6474.
23. 2]ethylene in diethyl ether: D. B. Denny and N. Tunkel, Chem. Ind. (London), 1959, 1383.
24. J. J. Gajewski, K. B. Peterson, J. R. Kagal and Y. C. Huang, J. Am. Chem. Soc., 1989, 111, 9078.
25. Y. Elemes and C. S. Foote, J. Am. Chem. Soc., 1992, 114, 8044.
26. F. Ruff and I. G. Csimadia, Organic Reactions, Equilibria, Kinetics and Mechanism, Elsevier, New York, 1994, pp. 233-236.
27. E. C. Ashby and J. J. Lin, J. Org. Chem., 1978, 43, 2567.