Formation of ketones from alkyl nitrites in the solid state

Chemistry Letters

Volumn , Issue 3, 1996, Pages 217-218

  Kinbara, Kazushi ^a   Takezaki, Hiroshi ^a   Kai, Akiyoshi ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030529429     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.217     Document Type: Article

References (13)

1. V. Ramamurthy, "Photochemistry in Organized and Constrained Media," VCH, New York (1991);
2. D. Hashizume, Y. Ohashi, K. Tanaka, and F. Toda, Synlett, 1993, 303.
3. P. Kabasakalian and E. R. Townley, J. Am. Chem. Soc., 84, 2711 (1962).
4. D. H. R. Barton, J. M. Beaton, L. E. Geller, and M. M. Pechet, J. Am. Chem. Soc., 83, 4076 (1961).
5. Isolated in a dimeric form.
6. D. H. R. Barton, R. H. Hesse, M. M. Pechet, and L. C. Smith, J. Chem. Soc., Perkin Trans, 1, 1979, 1159.
7. P. Kabasakalian, E. R. Townley, and M. D. Yudis, J. Am. Chem. Soc., 84, 2718 (1962).
8. In contrast, in benzene, the nitrite in entry 5, which did not undergo the Barton reaction, afforded a mixture of the corresponding alcohol and ketone in a ratio of 32:68 upon irradiation for 1.5 h.
9. As a result of the time-conversion analysis of the photoproducts, it was ascertained that the alcohol and ketone were directly produced from the corresponding nitrite upon irradiation.
10. -3, R=0.082, reflections used=1771.
11. M. D. Cohen, Angew. Chem., Int. Ed. Engl., 14, 386 (1975);
12. Y. Ohashi, A. Uchida, and A. Sekine, in "Reactivity in Molecular Crystals," ed by Y. Ohashi, Kodansha, Tokyo (1993) pp. 115-176.
13. PCMODEL was applied for the MM calculation.