Reactions of Carbonyl-Conjugated Alkynes with N-Bromosuccinimide and N-Iodosuccinimide in DMF/H2O and Methanol/Sulfuric Acid: Syntheses of Dihalo Diketones, Dihalo Ketoesters, and Dihalo Acetals

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4433-4437

  Heasley, Victor L ^a   Shellhamer, Dale F ^a   Chappell, Alfred E ^a   Cox, Jason M ^a   Hill, David J ^a   McGovern, Shanna L ^a   Eden, Cyndi C ^a   Kissel, Charles L ^b  

^a POINT LOMA NAZARENE UNIVERSITY   (United States)

^b CNC Development Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000684920     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980260n     Document Type: Article

References (13)

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2. Heasley, V. L.; Louie, T. J.; Luttrull, D. K.; Millar, M. D.; Moore H. B.; Nogales, D. F.; Sauerbrey, A. M.; Shevel, A. B.; Shibuya, T. Y., Stanley, M. S.; Shellhamer, D. F.; Heasley, G. E. J. Org. Chem. 1988, 53 2199.
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6. A reviewer has pointed out that our data are consistent with an enamide intermediate (see structure), perhaps accounting for the regiochemistry and the difference in reactivity between NBS and NIS. An enamide intermediate is also compatible with the acid-catalyzed mechanism. We have no evidence to support the formation of this intermediate. Chemical equations presented.
7. Moriarity, R. M.; Vaid, R. K.; Farid, P. J. Chem. Soc., Chem. Commun. 1987, 711.
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