ELECTROPHILIC SUBSTITUTION-REACTIONS OF BENZ[A]INDENO[1,2,3-CD]AZULENE

被引：4

作者：

TODA, T

MINABE, M

YOSHIDA, M

TOBITA, K

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Utsunomiya University

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 04期

关键词：

D O I：

10.1021/jo00291a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound (2) was prepared through the photochemical transformation of several triptycene derivatives. Electrophilic substitution reactions of 2 took place primarily at the 6-position: the Vilsmeier reaction gave the 6-formyl derivative in good yield; bromination afforded the 6-bromo derivative, accompanied by a small amount of the 6,11-dibromo compound; nitration yielded mainly the 6-nitro compound, with the 8-nitro derivative as a minor product. However, Friedel-Crafts type reactions did not give any acyl derivatives. Structures of the reaction products were confirmed by their NMR spectra. © 1990, American Chemical Society. All rights reserved.

引用

收藏

页码：1297 / 1300

页数：4

相关论文

共 50 条

[31] ELECTROPHILIC SUBSTITUTION-REACTIONS ON ZEOLITES .2. MECHANISM OF ANILINE ALKYLATION BY METHANOL [J].

MALYSHEVA, LV ;

KIKHTYANIN, OV ;

PAUKSHTIS, EA ;

IONE, KG .

IZVESTIYA SIBIRSKOGO OTDELENIYA AKADEMII NAUK SSSR SERIYA KHIMICHESKIKH NAUK, 1990, (03) :125-130

[32] SYNTHESIS AND ELECTROPHILIC SUBSTITUTION-REACTIONS OF FLUORINE CONTAINING ARYLGLYOXAL 2-ARYLHYDRAZONES [J].

JOSHI, KC ;

PATHAK, VN ;

SHARMA, S .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1985, 17 (02) :146-151

[33] RESONANCE ENERGIES OF THE ARENIUM IONS AND THEIR RELEVANCE TO THE ELECTROPHILIC SUBSTITUTION-REACTIONS [J].

AIHARA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (08) :2268-2273

[34] A prominent air pollutant, Indeno[1,2,3-cd]pyrene, enhances allergic lung inflammation via aryl hydrocarbon receptor [J].

Tzu-Hsuan Wong ;

Chon-Lin Lee ;

Hsiang-Han Su ;

Chin-Lai Lee ;

Chao-Chien Wu ;

Chin-Chou Wang ;

Chau-Chyun Sheu ;

Ruay-Sheng Lai ;

Sum-Yee Leung ;

Chi-Cheng Lin ;

Yu-Feng Wei ;

Chien-Jen Wang ;

Yu-Chun Lin ;

Hua-Ling Chen ;

Ming-Shyan Huang ;

Jeng-Hsien Yen ;

Shau-Ku Huang ;

Jau-Ling Suen .

Scientific Reports, 8

[35] ROLE OF CHARGE-TRANSFER IN AROMATIC ELECTROPHILIC SUBSTITUTION-REACTIONS [J].

GORB, LG ;

ABRONIN, IA ;

KORSUNOV, VA ;

ZHIDOMIROV, GM ;

LITVINOV, VP .

BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1984, 33 (05) :991-996

[36] Derivatives of 3,4,5,6-tetrahydro-6a,10b-diazaindeno[1,2,3-cd]azulene [J].

Nazarenko, KG ;

Shirokaya, TI ;

Shvidenko, KV ;

Tolmachev, AA ;

Tolmachev, AI ;

Ilchenko, AY .

KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (01) :126-128

[37] STEREOCHEMISTRY OF ELECTROPHILIC SUBSTITUTION-REACTIONS OF INDENYL-ORGANOTIN COMPOUNDS [J].

KASHIN, AN ;

BAKUNIN, VN ;

KHUTORYANSKII, VA ;

BELETSKAYA, IP ;

REUTOV, OA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 171 (03) :309-319

[38] A prominent air pollutant, Indeno[1,2,3-cd]pyrene, enhances allergic lung inflammation via aryl hydrocarbon receptor [J].

Wong, Tzu-Hsuan ;

Lee, Chon-Lin ;

Su, Hsiang-Han ;

Lee, Chin-Lai ;

Wu, Chao-Chien ;

Wang, Chin-Chou ;

Sheu, Chau-Chyun ;

Lai, Ruay-Sheng ;

Leung, Sum-Yee ;

Lin, Chi-Cheng ;

Wei, Yu-Feng ;

Wang, Chien-Jen ;

Lin, Yu-Chun ;

Chen, Hua-Ling ;

Huang, Ming-Shyan ;

Yen, Jeng-Hsien ;

Huang, Shau-Ku ;

Suen, Jau-Ling .

SCIENTIFIC REPORTS, 2018, 8

[39] HOMOAZULENE ELECTROPHILIC AROMATIC-SUBSTITUTION REACTIONS - PARALLELS TO THE CHEMISTRY OF AZULENE [J].

SCOTT, LT ;

SUMPTER, CA ;

ODA, M ;

ERDEN, I .

TETRAHEDRON LETTERS, 1989, 30 (03) :305-308

[40] ELECTROPHILIC SUBSTITUTION-REACTIONS OF BENZO[B]NAPHTHO[1,2-D]THIOPHENE [J].

DACKA, S ;

JANCZEWSKI, M .

POLISH JOURNAL OF CHEMISTRY, 1984, 58 (10-1) :1242-1244

← 1 2 3 4 5 →