Oligo(p-quinone methide)s bridged with thiophene rings. Novel oligomeric, quinonoid π-systems with high electron affinity

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8875-8878

  Kurata, Hiroyuki ^a   Hisamitsu, Akihito ^a   Oda, Masaji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER; QUINONE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY; STEREOCHEMISTRY;

EID: 0030733068     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10323-9     Document Type: Article

References (18)

1. Kawase, T.; Kurata, H.; Morikawa, T.; Oda, M.Tetrahedron Lett., 1993, 34, 3449.
2. Kurata, H.; Kawase T.; Oda, M. Chem. Lett., 1994, 2219.
3. For a review; The Chemistry of the quinonoid compounds Vol. 2 (Patai, S.; Rappoport, Z. ed.) Wiley, New York (1988).
4. Wagner, H. -U.; Gompper, R. The chemistry of the quinonoid compounds (Patai, S. ed), Chapt. 18 Quinone Methide, p 1145-1178 (1974).
5. b) Becker, H.-D., J. Org. Chem., 1967, 32, 2115.
6. c) Hünig S.; Schwarz, H. Liebigs Ann. Chem., 1956, 599, 131.
7. d) Musil, L; Koutek, B.; Verek, J.; Soucek, M. Coll. Czech. Chem. Commun., 1984, 49, 1949, and references cited therein.
8. Data obtained in our laboratory under the same conditions for 2a-c. See also Kawase, T.; Fujino, S.; Oda, M. Chem. Lett., 1990, 1683.
9. Gierke, W.; Harrer, W.; Kurreck, H.; Reusch, J. Tetrahedron Lett., 1973, 3681.
10. 5a: Acheson, R. M.; MacPhee, K. E.; Philpott, D. G.; Barltrop, J. A. J. Chem. Soc., 1956, 698.
11. 5b: Miyahara, Y. J. Heterocyctic. Chem., 1979, 1147.
12. 5c: Ahmed, M.; Meth-Cohn, O. J. Chem. Soc. (C), 1971, 2104.
13. 3) δ 7.14 (dd, J = 5.3, 1.1 Hz, 2H), 7.13 (s, 2H), 6.89 (dd, J = 5.3, 3.6 Hz, 2H), 6.80 (dd, J = 3.6, 1.3 Hz, 2H), 5.74 (s, 1H), 5.10 (s, 1H), 1.39 (s, 18H).
14. The integral area of these waves are nearly twice of the third reduction wave of 2c,d.
15. 2- are observed at δ 7.14 and 6.55 as singlets
16. 1H NMR signal are observable, although very complex due to the isomeric mixture similar to 2b
17. H= 1.50 G (20°C, THF)
18. 3COOD) δ 173.15, 170.93, 157.11, 156.94, 149.41, 145.28, 144.44, 143.38, 141.22, 135.51, 133.56, 35.92, 29.57.