The reaction of 2-chloro-4-nitrophenol and the isomeric chloronitrobenzenes with LDA under aryne-forming conditions

Tetrahedron

Volumn 54, Issue 50, 1998, Pages 15147-15154

  Tandel, Sagun ^a   Wang, Anlai ^a   Holdeman, Terra C ^a   Zhang, Hongming ^a   Biehl, Edward R ^a  

^a SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; NITROPHENOL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

EID: 0032506601     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00971-5     Document Type: Article

References (25)

1. 1. a. Hoffmann, R. W. Dehydrobenzene and Cycloalkanes; Academic Press: New York, 1967; pp. 134-150.
2. b. Fields, E. K. Arynes. In Organic Reactive Intermediates; McManus, S. P., Ed.; Academic Press: New York, 1973; pp. 449-508.
3. 2. Stiles, M; Miller, R. G. Burckhardt, U. J. Am. Chem. Soc. 1963, 85, 1792.
4. 3. Sakurai, H.; Sugiyama, H.; Kira, M. J. Organomet. Chem. 1982, 225, 163.
5. 4. Pyun, C.; Yoon, S.; Kim, J. H. J. Korean Chem. Soc. 1994, 38, 701-703. Chem. Abstr. 1994, 122, 9251.
6. 4. Pyun, C.; Yoon, S.; Kim, J. H. J. Korean Chem. Soc. 1994, 38, 701-703. Chem. Abstr. 1994, 122, 9251.
7. 5. Hoffmann, R. W.; Vargas-Numez, G. E.; Guhn, G.; Sieber, W. Chem. Ber. 1965, 98, 2074.
8. 6. Ritchie, C. D.; Sager, C. D. Prog. Phys. Org. Chem. 1964, 2, 323.
9. 7. Atkin, R. W.; Claxton, T. A. Trans. Faraday Soc. 1969, 91, 257.
10. 8. Fields, E. K.; Meyerson, S. Tetrahedron Lett. 1971, 719-722.
11. 9. Sheldrick, G. M. SHELXL93 Program for the Refinement of Crystal Structures, University of Goettingen, Germany, 1993.
12. 10. Pansegrau, P. D.; Rieker, W. F.; Meyers, A. I. J. Am. Chem. Soc. 1988, 110, 7178.
13. 11. Nieh, E.; Biehl, E. R. J. Org. Chem. 1969, 34, 3595.
14. 12. Ogata, Y.; Mibae, J. J. Org. Chem. 1962, 27, 2048.
15. 13. Ashby, E. C.; Deshpande, A. K.; Patil, G. S. J. Org. Chem. 1995, 60, 663
16. 14. Newkome, G. R.; Hager, D. C. J. Org. Chem. 1982, 47, 599
17. 15. Kimpe, N. D.; Yao, Z. P.; Schamp, N. Tetrahedron Lett. 1986, 27, 1707.
18. 16. Shen, C.; Ainsworth, C Tetrahedron Lett. 1979, 20, 89.
19. 17. Wittig, G.; Rentzea, C. N.; Rentzea, M. Liebigs Ann. Chem., 1971, 744, 8.
20. 18. Rondestvedt, C. S., Johnson, T. A. Johnson Synthesis, 1977, 12, 850.
21. 19. Friedrichsen, W.; Pagel, K, Progress in Heterocyclic Chemistry, Suschitzky, H. and Scriven, E. F. V. Eds; Pergamon: New York, 1995; Chapter 5.3 and references therein.
22. 20. Reuter, K. H.; Scott, W. J J. Org. Chem., 1993, 58, 4722.
23. 21. Ren, P.; Pan, S.; Dong, T.; Wu, S. Synth. Commun. 1996, 26, 3903.
24. 22. Borah, H.; Prajapati, D.; Sandhy, J.; Ghosh, A. C. Tetrahedron Lett. 1994, 35, 3167.
25. 23. Sekiya, M.; Takayama, S. Chem. Pharm. Bull., 1970, 18, 2146.