Generation of synthetic equivalents of benzdiynes from benzobisoxadisiloles

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7190-7197

  Chen, Ya Li ^a   Sun, Jiang Qin ^a   Wei, Xin ^a   Wong, Wai Yeung ^a   Lee, Albert W M ^a  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BENZENE; CHEMICAL ANALYSIS; FURAN RESINS; NAPHTHALENE;

ADDUCTS; CYCLOADDITION; SYNTHETIC EQUIVALENTS;

ORGANIC COMPOUNDS;

1,3 BENZDIYNE; 1,3 DIHYDRO 1,1,3,3 TETRAMETHYLNAPHTHY[2,3 C][1,2,5]OXADISILOLE; 1,3,5,7 TETRADIHYDRO 1,1,3,3,5,5,7,7 OCTAMETHYLBENZO[1,2 C:4,5 C']BIS[1,2,5]OXADISILOLE; 1,3,6,8 TETRADIHYDRO 1,1,3,3,6,6,8,8 OCTAMETHYLBENZO[1,2 C:3,4 C']BIS[1,2,5]OXADISILOLE; 1,4 BENZDIYNE; BENZENE DERIVATIVE; BENZOBISOXADISILOLE DERIVATIVE; FURAN DERIVATIVE; IODINE DERIVATIVE; NAPHTHALENE DERIVATIVE; OXYGEN; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; HYDROGENATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 5444227786     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049091z     Document Type: Article

References (47)

1. (a) Wittig, G. Naturwissenschaften 1942, 30, 696.
2. (b) Wittig, G.; Harborth, G. Ber. Dtsch. Chem. Ges. 1944, 77, 306, 316.
3. (c) Roberts, J. D.; Simmons, H. E.; Carlsmith, L. A.; Vaughan, C. W. J. Am. Chem. Soc. 1953, 75, 3290.
4. (d) Panar, M.; Roberts. J. D. J. Am. Chem. Soc, 1960, 82, 3629.
5. (e) Huisgen R.; Rist, H. Naturwissenschaften 1954, 41, 358.
6. (a) Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
7. (b) Hart, H. In The Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S, Ed.; John Wiley & Sons Ltd.: Chichester, UK, 1994; Chapter 18.
8. (c) Gilchrist, T. L. In The Chemistry of Functional Groups, Supplement C2; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, UK, 1983; Chapter 11.
9. (d) Cobas, A.; Diaz, M. T.; Escudero, S.; Prez, D.; Guitian, E.; Castedo, L. In Current Trends in Organic Synthesis; Scolastico, C., Nicotra, F., Eds.; Plenum Publishers: New York, 1999; pp 307-314.
10. (e) Yoshikawa, E.; Radhakrishnan, K V.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 7280-7286.
11. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827-5828.
12. (g) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. Synlett 2000, 7, 1061-1063.
13. (h) Wank, H. H.; Sand, W.; Winkler, M. Angew. Chem. 2003, 42, 502-528.
14. (i) Pellisier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730.
15. Pérez, D.; Guitián, E.; Castedo, L. J. Org. Chem, 1992, 57, 5911-5917.
16. Recent examples for the preparation and chemistry of benzynes. (a) Kitamura, T.; Yamane, M.; Inoue, K.; Tokuda, M.; Fukatsu, N.; Meng, Z.; Fujiwara, Y. J. Am. Chem. Soc. 1999, 121, 11674-11679.
17. (b) Matsumoto, T.; Hosoya, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1991, 32, 6735-6736.
18. (c) Kawabata, H.; Nishino, T.; Nishiyama, Y.; Sonoda, N. Tetrahedron Lett. 2002, 43, 4911-4913.
19. (d) Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sakamoto, T.; Otani, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514-8515.
20. (e) Duong, H. M.; Bendikov, M.; Steiger, D.; Zhang, Q.; Sonmez, G.; Yamada, J.; Wudl, F. Org. Lett. 2003, 5, 4433-4436.
21. (a) Kitamura, T.; Yamane, M. J. Chem. Soc., Chem. Commun. 1995, 983-984.
22. (b) Kitamura, T.; Todaka, M.; Fujiwara, Y. In Organic Syntheses; Roush, W. R., Ed.; Wiley: New York, 2000; Vol. 78, pp 104-112.
23. (a) Ye, S. S.; Li, W. K.; Wong, H. N. C. J. Am. Chem. Soc. 1996, 118, 2511-2512.
24. (b) Ye, S. S.; Wong, H. N. C. J. Org. Chem. 1997, 62, 1940-1954.
25. (c) Kitamura, T.; Todaka, M.; Shin-machi, I.; Fujowara, Y. Heterocycl. Commun. 1998, 4, 205-208.
26. (d) Okuma, K.; Shiki, K.; Shioji, K. Chem. Lett. 1998, 79-80.
27. (e) Winling, A.; Russell, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 3921-3923.
28. (f) Kitamura, T.; Fukatsu, N.; Fijiwara, Y. J. Org. Chem. 1998, 63, 7579-8581.
29. (g) Liu, J. H.; Chan, H. W.; Xue, F.; Wang, G. G.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 1999, 64, 1630-1634.
30. (h) Yick, C. Y.; Chan, S. H.; Woy, H. N. Tetrahedron Lett. 2000, 4, 5957-5961.
31. Kitamura, T.; Meng, Z.; Fujiwara, T. Tetrahedron Lett. 2000, 41, 6611-6614.
32. (a) Sattelmeyer, K. W.; Stanton, J. F. J. Am. Chem. Soc. 2000, 122, 8220-8227.
33. (b) Bettinger, H. F.; Schleyer, P. R.; Schaefer, H. F. J. Am. Chem. Soc. 1999, 121, 2829-2835.
34. (c) Zahradnik, R.; Hoba, P.; Burcl, R.; Andes, H. B. J.; Radziszewski, J. G. THEOCHEM 1994, 3, 335-349.
35. (d) Radom, L.; Nobes, R. H.; Underwood, D. J. Pure Appl. Chem. 1986, 1, 75-88.
36. (a) Sato, T.; Nino, H.; Yabe, A. J. Am. Chem. Soc. 2003, 125, 11936-11941.
37. (b) Sato, T.; Arulmozhiraja, S.; Nino, H.; Sasaki, S.; Yabe, A. J. Am. Chem. Soc. 2002, 124, 4512-4521.
38. (a) Hart, H.; Lai, C.; NwoRogu, G. C.; Shamonilian, S. Tetrahedron 1987, 43 5203-5224.
39. (b) Stephen, L.; Lucas, E. A.; Dewan, J. C. J. Am. Chem. Soc. 1987, 109, 4396-4397.
40. (c) Hsu, D. P.; Lucas, E. A.; Buchwald, L. Tetrahedron Lett. 1990, 31, 5563-5566.
41. Fink, W. Helv. Chim. Acta 1974, 57, 1010-1015.
42. A preliminary communication: Chen, Y. L.; Zhang, H.; Wong, W. Y.; Lee, A. W. M. Tetrahedron Lett. 2002, 43, 2259-2262.
43. Collins, I.; Suschitzk, H. J. Chem. Soc. (C) 1969, 2337-2341.
44. Daly, J. J.; Sanz, F. J. Chem. Soc., Dalton. Trans. 1973, 2474-2475.
45. (a) Mueller, P.; Schaller, J. P. Chimia 1986, 40, 430-431.
46. (b) Wang, X. M.; Hou, X. L.; Zhou, Z. Y.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 1993, 58, 7498-7506.
47. Kitamura, T.; Fukatsu, N.; Fujiwara, Y. J. Org. Chem. 1998, 63, 8579-8581.