Oxidation of electron-deficient anilines by HOF. A route to nitro-containing compounds for molecular electronic devices

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3405-3406

  Dirk, Shawn M ^a   Mickelson, Edward T ^a   Henderson, Jay C ^a   Tour, James M ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001235918     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006539j     Document Type: Article

References (19)

1. (a) Tour, J. M. Acc. Chem Res. In press.
2. (b) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550.
3. (c) Chen, J.; Wang, W.; Reed, M. A.; Rawlett, A. M.; Price, D. W.; Tour, J. M. Appl. Phys. Lett. 2000, 77, 1224.
4. (a) Howe, G. R.; Hiatt, R. R. J. Org. Chem. 1970, 35, 4007.
5. (b) Emmons, W. D. J. Am Chem. Soc. 1957, 79, 5528.
6. (c) Suresh, S.; Joseph, R.; Jayachandran, B.; Pol, A. V.; Vinod, M. P. Tetrahedron 1995, 51, 11305.
7. Nielson, A. T.; Atkins, R. L.; Norris, W. P.; Coon, C. L.; Sitzmann, M. E. J. Org. Chem. 1980, 45, 2341.
8. McKillop, A.; Tarbin, J. A. Tetrahedron 1987, 43, 1753.
9. Zabrowski, D. L.; Moormann, A. E.; Beck, K. R., Jr. Tetrahedron Lett. 1988, 29, 4501.
10. Emmons, W. D. J. Am. Chem. Soc. 1954, 76, 3470.
11. (a) Appelman, E. H.; Thompson, R. C. J. Am. Chem Soc 1984, 106, 4167.
12. (b) Poll, W.; Pawelke, G.; Mootz, D.; Appelman, E. H. Angew. Chem., Int. Ed. Engl. 1988, 27, 392.
13. (c) Dunkelberg, O.; Haas, A.; Klapdor M. F., Mootz, D.; Poll, W.; Appelman, E. H. Chem. Ber. 1994, 127, 1871.
14. Kol, M.; Rozen, S. J. Chem. Soc., Chem. Commun. 1991, 8, 567.
15. Appelman, E. H.; Dunkelberg, O.; Kol, M. J. Fluorine Chem. 1992, 56, 199.
16. 2/He mixtures and purchased them as the mixture from Matheson. The latter procedure is simpler.
17. Standard cubic centimeter per minute (seem).
18. 2O → HOF + HF reaction was complete, our explosion problem ceased.
19. Dunkelberg, O.; Haas, A.; Klapdor, M. F.; Mootz D.; Poll, W.; Appelman, E. H. Chem. Ber. 1994, 127, 1871.