Electrophilic Aromatic Bromination Using Bromodimethylsulfoniuin Bromide Generated in Situ

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4321-4326

  Majetich, George ^a   Hicks, Rodgers ^a   Reister, Steven ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001738468     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970135w     Document Type: Article

References (17)

1. (a) Electrophilic Halogenation: Reaction Pathways Involving Attack by Electrophilic Halogens on Unsaturated Compounds; de la Mare. P. B. D., Ed.; Cambridge University Press: London, 1976.
2. (b) Berliner, E. J. Chem. Ed. 1996, 43, 124.
3. 7
4. Olah, G.; Vankar, D.; Arvanaghi, M.; Prekash, G. Synthesis 1979, 720.
5. Chow, Y.; Baker, B. Synthesis 1982, 648.
6. The following mechanism accounts for the formation of bromo-sulfonium bromide from DMSO and HBr; see: Mislow, K.; Simmons, T.; Melillo, J.; Ternay, A. J. Am. Chem. Soc. 1964, 86, 1452. chemical equation presented.
7. Landini, D.; Montari, F. J. Chem. Soc., Chem. Commun. 1968, 86.
8. Megyeri, G.; Keve, T. Synth. Commun. 1989, 19, 3415.
9. Olah, G.; Arvanaghi, M.; Vankar, Y. Synthesis 1979, 721.
10. Floyd, M.; Du, M.; Fabio, P.; Jacob, L.; Johnson, B. J. Org. Chem. 1984, 50, 5022.
11. Fletcher, T.; Pan, H. J. Am. Chem. Soc. 1956, 78, 4812.
12. Although 2-methylnaphthalene failed to react with 1, even with heating, it reacted slowly with elemental bromine to give 1-bromo-2-methylnaphthalene as well as other inseparable byproducts.
13. Adams, R.; Marvel, C. S. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I, p 128.
14. Reference 1a, p 126.
15. For the reactions of 31 with epoxides and enamines, see: Olah, G. A.; Vankar, Y. D.; Arvanaghi, M. Tetrahedron Lett. 1979, 38, 3653.
16. Attempts to extend this methodology for the preparation of aryl iodides failed as the iododimethyl sulfonium iodide, generated in situ, rapidly decomposes to produce molecular iodine.
17. Others have recently independently reported the regiospecific bromination of benzene derivatives with DMSO - HBr. However, this report lacks detailed experimental procedures so as to allow the duplication of their results and presents an unlikely mechanism. See: Srivastava, S. K.; Chauhan, P. M. S.; Bhaduri, A. P. J. Chem. Soc., Chem. Commun. 1996, 2679.