Reactions of vinylidenecyclopropanes with diphenyl diselenide in the presence of AIBN and further transformation to produce new naphthalene derivatives

Journal of Organic Chemistry

Volumn 71, Issue 5, 2006, Pages 1920-1923

  Shi, Min ^a,b   Lu, Jian Mei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HYDROGEN PEROXIDE; NAPHTHALENE; REACTION KINETICS;

DICHLOROMETHANE; VINYLIDENCYCLOPROPANES;

PARAFFINS;

CYCLOPROPANE DERIVATIVE; DICHLOROMETHANE; DIPHENYL SELENIDE; HYDROGEN PEROXIDE; METHYLENECYCLOPROPANE DERIVATIVE; NAPHTHALENE DERIVATIVE; SELENIDE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; FRIEDEL CRAFTS REACTION; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 33644655936     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0522613     Document Type: Article

References (31)

1. (a) Mizuno, K.; Sugita, H.; Hirai, T.; Maeda, H.; Otsuji, Y.; Yasuda, M.; Hashiguchi, M.; Shima, K. Tetrahedron Lett. 2001, 42, 3363.
2. (b) Mizuno, K.; Nire, K.; Sugita, H.; Otsuji, Y. Tetrahedron Lett. 1993, 34, 6563.
3. (c) Sasaki, T.; Eguchi, S.; Ogawa, T. J. Am. Chem. Soc. 1975, 97, 4413.
4. (d) Pasto, D. J.; Chen, A. F.-T.; Binsch, G. J. Am. Chem. Soc. 1973, 95, 1553.
5. (e) Pasto, D. J.; Chen, A. F.-T. J. Am. Chem. Soc. 1971, 93, 2526.
6. (f) Pasto, D. J.; Borchardt, J. K.; Fehlper, T. P.; Baney, H. F.; Schwartz, M. E. J. Am. Chem. Soc. 1976, 98, 526.
7. (g) Pasto, D. J.; Chen, A. F.-T.; Clurdaru, G.; Paquette, L. A. J. Org. Chem. 1973, 38, 1015.
8. (h) Pasto, D. J.; Borchardt, J. K. J. Am. Chem. Soc. 1974, 96, 6937.
9. (a) Mizuno, K.; Sugita, H.; Hirai, T.; Maeda, H. Chem. Lett. 2000, 1144.
10. (b) Mizuno, K.; Maeda, H.; Sugita, H.; Nishioka, S.; Hirai, T.; Sugimoto, A. Org. Lett. 2001, 3, 581.
11. (c) Mizuno, K.; Sugita, H.; Kamada, T.; Otsuji, Y. Chem. Lett. 1994, 449.
12. (d) Maeda, H.; Hirai, T.; Sugimoto, A.; Mizuno, K. J. Org. Chem. 2003, 68, 7700.
13. (e) Pasto, D. J.; Miles, M. F. J. Org. Chem. 1976, 41, 425.
14. (f) Pasto, D. J.; Miles, M. F.; Chou, S.-K. J. Org. Chem. 1977, 42, 3098.
15. (g) Xu, G.-C; Ma, M.; Liu, L.-P.; Shi, M. Synlett 2005, 1869.
16. Selected monographs: (a) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon: Oxford, 1986.
17. (b) Organoselenium Chemistry; Black, T. G., Ed.; Oxford: New York, 1999.
18. (c) Organoselenium Chemistry; Wirth, T., Ed.; Springer: Berlin, 2000.
19. Yao, Q.-W.; Kinney, E. P.; Zheng, C. Org. Lett. 2004, 6, 2997.
20. Shi, M.; Lu, J.-M. Synlett 2005, 2352.
21. Pasto, D. J.; Miels, F. M. J. Org. Chem. 1976, 41, 2068.
22. Walborsky, H. M.; Chen, J.-C. J. Am. Chem. Soc. 1970, 92, 7573.
23. (a) Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 2135.
24. (b) Liu, L.-P.; Shi, M. Chem. Commun. 2004, 2878.
25. w, 0.0408, 0.0769.
26. For a recent review, see: Reich, H. J. Organoselenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987; pp 365-394.
27. (a) Denmark, S. E.; Chen, C.-T. Tetrahedron lett. 1994, 55, 4327.
28. (b) Freund, T.; Scherf, U.; Mullen, K. Angew. Chem. 1994, 33, 2424.
29. (c) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C-H.; Chou, I.-C.; Hon, S.-W J. Am. Chem. Soc. 1997, 46, 11341.
30. (a) Applequist, D. E.; Nickel, G. W. J. Org. Chem. 1979, 44, 321.
31. (b) Brown, H. C.; Rao, C. G.; Ravindranathan, M. J. Am. Chem. Soc. 1978, 100, 7946.