Photoreactions of N-tosyldihydrodiazaazulanones to form diazaazulanones and ionic pairs between p-toluenesulfonate anion and tropyliumions

Heterocycles

Volumn 51, Issue 8, 1999, Pages 1775-1778

  Doi, Tadayuki ^a   Ishiguro, Hiroyuki ^a   Sato, Michie ^a   Saito, Katsuhiro ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; HETEROCYCLIC COMPOUND; TOLUENESULFONAMIDE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; IRRADIATION; PHOTOREACTIVITY; PROTON TRANSPORT;

EID: 0033179884     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8569     Document Type: Article

References (13)

1. K. Ito, K. Saito, S. Takeuchi, and K. Takahashi, Heterocycles, 1992, 34, 1415.
2. O. L. Chapman and G. W. Borden, Proc. Chem. Soc., 1963, 211; A. P. ter Borg and H. Kloosterziel, Rec. Trav. Chim. Pays-Bus, 1965, 84, 241; R. W. Murray and M. L. Kaplan, J. Am. Chem. Soc., 1966, 88, 3527; S. L. Mattes and S. Farid, J. Am. Chem. Soc., 1983, 105, 1386; G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1984, 106, 6870.
3. O. L. Chapman and G. W. Borden, Proc. Chem. Soc., 1963, 211; A. P. ter Borg and H. Kloosterziel, Rec. Trav. Chim. Pays-Bus, 1965, 84, 241; R. W. Murray and M. L. Kaplan, J. Am. Chem. Soc., 1966, 88, 3527; S. L. Mattes and S. Farid, J. Am. Chem. Soc., 1983, 105, 1386; G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1984, 106, 6870.
4. O. L. Chapman and G. W. Borden, Proc. Chem. Soc., 1963, 211; A. P. ter Borg and H. Kloosterziel, Rec. Trav. Chim. Pays-Bus, 1965, 84, 241; R. W. Murray and M. L. Kaplan, J. Am. Chem. Soc., 1966, 88, 3527; S. L. Mattes and S. Farid, J. Am. Chem. Soc., 1983, 105, 1386; G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1984, 106, 6870.
5. O. L. Chapman and G. W. Borden, Proc. Chem. Soc., 1963, 211; A. P. ter Borg and H. Kloosterziel, Rec. Trav. Chim. Pays-Bus, 1965, 84, 241; R. W. Murray and M. L. Kaplan, J. Am. Chem. Soc., 1966, 88, 3527; S. L. Mattes and S. Farid, J. Am. Chem. Soc., 1983, 105, 1386; G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1984, 106, 6870.
6. O. L. Chapman and G. W. Borden, Proc. Chem. Soc., 1963, 211; A. P. ter Borg and H. Kloosterziel, Rec. Trav. Chim. Pays-Bus, 1965, 84, 241; R. W. Murray and M. L. Kaplan, J. Am. Chem. Soc., 1966, 88, 3527; S. L. Mattes and S. Farid, J. Am. Chem. Soc., 1983, 105, 1386; G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1984, 106, 6870.
7. K. Ito, Y. Hara, R. Sakakibara, and K. Saito, Heterocycles, 1995, 41, 1675; K. Ito, K. Saito, and K. Takahashi, Heterocycles, 1993, 36, 1459.
8. K. Ito, Y. Hara, R. Sakakibara, and K. Saito, Heterocycles, 1995, 41, 1675; K. Ito, K. Saito, and K. Takahashi, Heterocycles, 1993, 36, 1459.
9. -1. UV (MeOH): 223 nm (log ε ,4.43), 249 (4.36), 345 (3.85).
10. -3, R= 0.051, Rw= 0.067 for 6509 observed reflection.
11. 2CO 20.70 1.06 0.25 0.81 THF 7.58 0.84 0.17 0.67 * C. G. Swain, R. B. Moseley, and D. E. Bown, J. Am. Chem. Soc., 1955, 77, 3731.
12. K. Ogura, K. Ohtsuka, M. Nakamura, N. Yahata, K. Takahashi, and H. Iida, Tetrahedron Lett., 1985, 26, 2455.
13. 2. The photoreaction was strongly promoted by humidity in THF (Run 1) and by oxygen (Run 3).