Synthesis of 1,2,9,10-tetrahydroxy[2.2]metacyclophanes via pinacol coupling reaction of 1,3-benzenedicarboxyaldehydes

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2573-2580

  Sahade, Daniel A ^a   Tsukamoto, Ken Ichi ^a   Thiemann, Thies ^a   Sawada, Tsuyoshi ^a   Mataka, Shuntaro ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALUMINUM; ISOPHTHALIC ACID; METACYCLOPHANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MOLECULAR INTERACTION; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 0033605197     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00055-1     Document Type: Article

References (19)

1. Yamato, T.; Fujita, K.; Ando, T.; Ide, S.; Nagano, Y.; Tashiro, M. J. Chem. Res. (S), 1996, 264-265.
2. Krois, D.; Langer, E.; Lehner, H. Tetrahedron, 1980, 36, 1345-1351.
3. Gschwend, H. W.; J. Am. Chem. Soc., 1972, 94, 8430-8437.
4. Griffin, R. W. Jr., Baughman, R. W.; Ramey, C. E. Tetrahedron Lett., 1968, 5419-5421.
5. Sahade, D. A.; Mataka, S.; Sawada, T.; Tsukinoki, T.; Tashiro, M. Tetrahedron Lett., 1997, 38, 3745-3746.
6. Tsukinoki, T.; Kawaji, T.; Hashimoto, I.; Etoh, T.; Sahade, D. A.; Tashiro, M. Eng. Sci. Reports, Kyushu Univ., 1997, 19, 15-18.
7. Sahade, D. A.; Kawaji, T.; Sawada, T.; Mataka, S.; Thiemann, T.; Tsukinoki, T.; Tashiro, M. J. Chem. Res. (S), in press.
8. The stabilization of structures by CH-π interaction has been described in the literature; e.g., Yamato, T.; Miyazawa, A.; Tashiro, M. J. Chem. Soc., Perkin Trans, 1, 1993, 3127-3137 and references cited therein.
9. This kind of reaction-promoting (or -directing) aluminium-oxygen complexes have been reported recently: Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc., 1998, 120, 5327-5328.
10. Johnstone, R. A.; Rose, M. E. Tetrahedron, 1979, 35, 2169-2173.
11. Imamoto, T.; Ono, M. Chem. Lett., 1987, 501-502.
12. Mukaiyama, T.; Sato, T.; Harna, J. Chem. Lett., 1973, 1041-1044.
13. Handa, Y.; Inanaga, J. Tetrahedron Lett., 1987, 28, 5717-5718.
14. Mitchell, R.; Boekelheide, V. J. Am. Chem. Soc., 1974, 96, 1547-1557.
15. Tashiro, M.; Yamato, T. Org. Prep. Proced. Int., 1981, 13, 1-7.
16. Firouzabadi, H.; Ghaderi, E. Tetrahedron Lett., 1978, 839-840.
17. Chu, K. Y.; Griffiths, J.; Ward, D. J. Chem. Res. (M), 1981, 3701-3721.
18. Tashiro, M.; Yamato, T. Synthesis , 1978, 435-436.
19. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Cryst., 1994, 27, 435.