Para Photoaddition of N-Methyltriazolinedione to Benzene. Synthesis of Energy-Rich Azo Compounds Comprising Benzene + N2

Journal of the American Chemical Society

Volumn 111, Issue 26, 1989, Pages 9247-9249

  Hamrock, Steven J ^a   Sheridan, Robert S ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRIAZOLINE DERIVATIVE;

DRUG SYNTHESIS; LETTER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0024806195     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00208a028     Document Type: Article

References (22)

1. (a) Wender, P. A.; Von Geldern, T. W.; Levine, B. H. J. Am. Chem. Soc. 1988, 110, 4858 and references therein. (b) Mattay, J. J. Photochem. 1987, 37, 167 and references therein.
2. (a) McCullough, J. J. Chem. Rev. 1987, 87, 811 and references therein. (b) Yang, N. C.; Masnovi, J.; Chiang, W.; Wang, T.; Shou, H.; Yang, D. H. Tetrahedron 1981, 37, 3285.
3. (a) Adam, W.; De Lucchi, O. Angew. Chem., Int. Ed. Engl. 1980, 19, 762. (b) Burrage, M. E.; Cookson, R. C.; Gupte, S. S.; Stevens, I. D. R. J. Chem. Soc., Perkin Trans. 2 1975, 1325.
4. (a) Kjell, D. P.; Sheridan, R. S. J. Am. Chem. Soc. 1984, 106, 5368. (b) Kjell, D. P.; Sheridan, R. S. J. Photochem. 1985, 28, 205.
5. Hamrock, S. J.; Sheridan, R. S. Tetrahedron Lett, 1988, 29, 5509.
6. (a) Chang, M. H.; Dougherty, D. A. J. Org. Chem. 1981, 46, 4092. (b) Amey, R. L.; Smart, B. E. J. Org. Chem. 1981, 46, 4090. (c) Snyder, G. J.; Dougherty, D. A. J. Am. Chem. Soc. 1989, 111, 3927.
7. The greater lability of 4 (t1/2= 1 h at 0 °C) compared to 2 and 3 is consistent with the expected gain in aromaticity on cycloreversion. See: Hess, B. A., Jr.; Schaad, L. J.; Herndon, W. W.; Biermann, D.; Schmidt, W. Tetrahedron 1981, 37, 2983.
8. For alternate approaches to adducts similar to 2–4, see: Askani, R.; Schneider, W. Chem. Ber. 1983, 116, 2355.
9. (a) Jensen, F.; Foote, C. S. J. Am. Chem. Soc. 1987, 109, 6376. (b) Smonou, I.; Orfanopoulos, M.; Foote, C. S. Tetrahedron Lett. 1988, 29, 2769. (c) Clennan, E. L.; Earlywine, A. D. J. Am. Chem. Soc. 1987, 109, 7104.
10. Mattay, J. Tetrahedron 1985, 41, 2393, 2405.
11. Weller, A. Z. Phys. Chem. NF 1982, 133, 93.
12. Houk, K. N. Pure Appl. Chem. 1982, 54, 1633.
13. Bryce-Smith and Gilbert have shown that photoadditions of this nature, where the dienophile is excited, are actually formally allowed by MO correlations. Bryce-Smith, D.; Gilbert, A. Tetrahedron 1976, 32, 1309.
14. (a) Epiotis, N. D.; Yates, R. L. J. Org. Chem. 1974, 39, 3150. (b) Inagaki, S.; Hirabayashi, Y. Chem. Lett. 1978, 135.
15. (a) Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Interscience: New York, 1970. (b) Jordan, K. D.; Burrow, P. D. Acc. Chem. Res. 1978, 11, 341. (c) Gleiter, R.; Schafer, W.; Wamhoff, H. J. Org. Chem. 1985, 50, 4375.
16. Barfield, M.; Chakrabarty, B. Chem. Rev. 1969, 69, 757.
17. This is a modified procedure of Adam et al.: Adam, W.; Arias, L. A.; DeLucchi, O. Synthesis 1981, 543.
18. Kjell, D. P.; Sheridan, R. S. J. Am. Chem. Soc. 1986, 108, 4111. (b) Burger, U.; Mentha, Y.; Thorel, P. J. Helv. Chim. Acta 1986, 69, 670.
19. A methylated derivative of the urazole corresponding to this ring system has been isolated: Christl, M.; Kemmer, P.; Mattauch, B. Chem. Ber. 1986, 119, 960.
20. Benson, S. W. Thermochemical Kinetics, 2nd, ed.; Wiley: New York, 1976.
21. For comparison with related azo systems, see: (a) Allred, E. L.; Voorhees, K. J. J. Am. Chem. Soc. 1971, 93, 1300. (b) Zimmerman, H. E.; Boettcher, R. J.; Buehler, N. E.; Keck, G. E.; Steinmetz, M. G. J. Am. Chem. Soc. 1976, 98, 7680.
22. Berson, J. A.; Olin, S. S.; Petrillo, E. W., Jr.; Bickart, P. Tetrahedron 1974, 30, 1639.