Formation of 3-Bromo-1,5- And -1,7-Azulenequinones from 1-Alkyl- and 1-Phenylazulenes by Substituent Extrusion on the Bromine-Oxidation in Aqueous THF. Remarkable Substituent Effects on the Product Distribution

Journal of the Chinese Chemical Society

Volumn 43, Issue 4, 1996, Pages 301-304

  Wakabayashi, Hidetsugu ^a   Takano, Akifumi ^a   Shindo, Kimio ^a   Yasunami, Masafumi ^b   Chen, Jhy An ^c   Yang, Paw Wang ^c   Nozoe, Tetsuo ^d  

^a JOSAI UNIVERSITY   (Japan)

^b NIHON UNIVERSITY   (Japan)

^c NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^d KAO CORPORATION   (Japan)

Author keywords

1 alkylazulenes; Azulenequinones; Bromine oxidation; Substituent extrusion

Indexed keywords

EID: 0346471478     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.199600044     Document Type: Article

References (10)

1. Partly presented by Nozoe, T., at 4th Towa University International Symposium, Fukuoka, Nov. 1994, Abstr. pp. 13-18; Wakabayashi, H.; Shindo, K.; Ishikawa, S.; Yasunami, M.; Nozoe, T. 24th Symposium on Structural Organic Chemistry, Oct. 1994, Fukuoka, Abstr. 2P65.
2. Partly presented by Nozoe, T., at 4th Towa University International Symposium, Fukuoka, Nov. 1994, Abstr. pp. 13-18; Wakabayashi, H.; Shindo, K.; Ishikawa, S.; Yasunami, M.; Nozoe, T. 24th Symposium on Structural Organic Chemistry, Oct. 1994, Fukuoka, Abstr. 2P65.
3. Nozoe, T.; Wakabayashi, H.; Shindo, K.; Kurihara, T.; Ishikawa, S.; Kageyama, M. Chem. Lett. 1995, 25.
4. Nozoe, T.; Wakabayashi, H.; Shindo, K.; Yasunami, M. Chem. Lett. 1995, 439.
5. Yang, P.-W.; Yasunami, M.; Takase, K. Tetrahedron Lett. 1971, 4275; Amemiya, T.; Yasunami, M.; Takase, K. Chem. Lett. 1977, 587; Kitamori, Y.; Yasunami, M.; Hioki, T.; Kikuchi, I.; Takase, K. Bull. Chem. Soc. Jpn. 1992, 65, 2131.
6. Yang, P.-W.; Yasunami, M.; Takase, K. Tetrahedron Lett. 1971, 4275; Amemiya, T.; Yasunami, M.; Takase, K. Chem. Lett. 1977, 587; Kitamori, Y.; Yasunami, M.; Hioki, T.; Kikuchi, I.; Takase, K. Bull. Chem. Soc. Jpn. 1992, 65, 2131.
7. Yang, P.-W.; Yasunami, M.; Takase, K. Tetrahedron Lett. 1971, 4275; Amemiya, T.; Yasunami, M.; Takase, K. Chem. Lett. 1977, 587; Kitamori, Y.; Yasunami, M.; Hioki, T.; Kikuchi, I.; Takase, K. Bull. Chem. Soc. Jpn. 1992, 65, 2131.
8. 2), 6.90 (1H, ddd, J = 12.1, 2.8, 1.2 Hz, H-6), 7.03 (1H, dd, J = 2.8, 0.8 Hz, H-4), 7.14 (1H, dd, J = 12.1, 7.8 Hz, H-7), 7.23 (1H, ddd, J = 7.8, 1.2, 0.8 Hz, H-8), 9.73 (1H, s, CHO).
9. 3, Z = 4. Data were collected on a Nonius CAD4 diffractometer using Mo-Kα (0.7093 Å) radiation at 298°K. Reflections measured; 2424; reflections used: 2258. The final refinement converted with R = 0.040 and Rw = 0.041. Selected bond distances (Å): Br-C1 1.876(4), C1-C2 1.468(6), C1-C15 1.326(6), C2-C3 1.355(6), C2-C8 1.431(6), C3-C4 1.452(7), C4-C5 1.441(7), C4-O1 1.246(6), C5-C6 1.337(7), C6-C7 1.432(7), C7-C8 1.355(6), C8-C9 1.538(6), C9-C10 1.517(7), C9-C15 1.523(6), C9-O2 1.429(6), C10-C11 1.502(8), C11-C12 1.545(8), C12-C13 1.511(8), C13-C14 1.509(8), C14-C15 1.501(7).
10. Johnson, C. K. "ORTEP II, Report ORNL-5138", Oak Ridge National Laboratory, Tennessee, USA (1976).