Synthesis of carboalkoxychloro- and bromodiazirines

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7359-7362

  Martinu, Tomas ^a   Dailey, William P ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; DECHLORINATION; HALOGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

BROMODIAZIRINES; CARBOALKOXYCHLORO; ORGANIC SYNTHESIS;

CARBONYLATION;

AMIDINE; AZIRINE DERIVATIVE; BROMIDE; BROMODIAZIRINE; CHLORIDE; FORMAMIDINE; N,N,N' TRICHLOROAMIDINE; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHLORINATION; ORGANIC CHEMISTRY; REDUCTION; SYNTHESIS;

DIAZOMETHANE; HYDROCARBONS, BROMINATED; HYDROCARBONS, CHLORINATED; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 5444255102     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040194r     Document Type: Article

References (17)

1. Schmitz, E. In Chemistry of Diazirines; Liu, M. T. H., Ed.; CRC Press: Boca Raton, FL, 1987; Vol. I, p 57.
2. Schöllkopf, U.; Gerhart, F.; Reetz, M.; Frasnelli, H.; Schumacher, H. Liebigs Ann. Chem. 1968, 776, 204.
3. For review of halodiazirine exchange reactions, see: Creary, X. Acc. Chem. Res. 1992, 25, 31.
4. (a) Likhotvorik, I.; Zhu, Z.; Tae, E. L.; Tippmann, E.; Hill, B. T.; Platz, M. S. J. Am. Chem. Soc. 2001, 123, 6061.
5. (b) Tippmann, E. M.; Holinga, G.; Platz, M. Org. Lett. 2003, 5, 4919.
6. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396.
7. Moss, R. A.; Wlostowska, J.; Guo, W.; Fedorynski, M.; Springer, J. P.; Hirshfield, J. M. J. Org. Chem. 1981, 46, 5050.
8. A similar disproportionation of N,N'-dichlorobenzamidine was described in ref 6.
9. (a) Coon, C. L.; Ross, D. L.; Hill, M. E. Tetrahedron Lett. 1966, 3537.
10. (b) Markovskii, L. N.; Pinchuk, A. M.; Khimchenko, T. V. J. Org. Chem. USSR (Engl. Transl.) 1969, 5, 1283.
11. (c) Coon, C. L. Trichloroamidines, useful as chlorinating agents, bleaches, bactericides. U.S. Patent 3,526,664, September 1, 1970.
12. (d) Coon, C. L. Polychlorobisamidines. U.S. Patent 3,673,252, June 27, 1972.
13. (e) Davydov, A. V.; Kretov, A. E. Zh. Vses. Khim. Ova. im. D. I. Mendeleeva 1981, 26, 478.
14. Reductive defluorination of tetrafluoroformamidine with 2 equiv of potassium iodide in acetonitrile was reported to yield difluorodiazirine. Rebertus, R. L.; Toren, P. E. J. Org. Chem. 1967, 32, 4045.
15. Terpinski, J.; Denney, D. Z.; Beveridge, R.; Cox, D. P.; Moss, R. A. Magn. Reson. Chem. 1987, 25, 923.
16. Cyclopropanecarboxylates 10a,c: (a) Seyferth, D.; Woodruff, R. A.; Mueller, D. C.; Lambert, R. L. J. Organomet. Chem. 1972, 43, 55.
17. (b) Mueller, C.; Stier, F.; Weyerstahl, P. Chem. Ber. 1977, 110, 124.