Synthesis of benzo[c]selenophene and derivatives via new routes

被引：14

作者：

Aqad, E ^{[1
]}

Lakshmikantham, MV ^{[1
]}

Cava, MP ^{[1
]}

Broker, GA ^{[1
]}

Rogers, RD ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 14期

关键词：

D O I：

10.1021/ol034791w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Benzo[c]selenophene has been generated via facile bromination-dehydrobromination as well as oxidation of the 1,3-dlhydrobenzo[c]selenophene. Benzo[c]selenophene thus generated has been lithiated in situ and treated with CICOOEt to give the first functionalized derivative subject to X-ray crystallographic analysis.

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收藏

页码：2519 / 2521

页数：3

相关论文

共 14 条

[1] Condensed thiophenes and selenophenes: Thionyl chloride and selenium oxychloride as sulfur and selenium transfer reagents [J].

Amaresh, RR ;

Lakshmikantham, MV ;

Baldwin, JW ;

Cava, MP ;

Metzger, RM ;

Rogers, RD .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2453-2458

[2] SIMPLE SYNTHETIC ROUTE TO BENZO[C]THIOPHENE AND NAPHTHO[C]THIOPHENES [J].

CAVA, MP ;

POLLACK, NM ;

MAMER, OA ;

MITCHELL, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (25) :3932-&

[3] ELECTRONIC-STRUCTURE, AROMATIC CHARACTER, AND CHEMICAL REACTIVITY OF ORTHO-QUINONOIDAL HETEROCYCLES [J].

CHACKO, E ;

BORNSTEIN, J ;

SARDELLA, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8248-8251

[4] ELECTROCHEMICAL AND OPTOELECTROCHEMICAL PROPERTIES OF POLY(ISOTHIANAPHTHENE) [J].

COLANERI, N ;

KOBAYASHI, M ;

HEEGER, AJ ;

WUDL, F .

SYNTHETIC METALS, 1986, 14 (1-2) :45-52

[5]

Dean F. M., 1984, COMPREHENSIVE HETERO, V4, P531, DOI DOI 10.1016/B978-008096519-2.00060-6

[6]

FRIEDRICHSEN W, 1980, ADV HETEROCYCL CHEM, V26, P135

[7]

GEYER W, 1994, METHODEN ORG CHEM E, V6, P275

[8] Synthesis and isolation of some benzo[c]tellurophenes [J].

Huang, ZZ ;

Lakshmikantham, MV ;

Lyon, M ;

Cava, MP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5413-5415

[9]

IDDON B, 1972, ADVAN HETEROCYCL CHE, V14, P331

[10] THE ELECTRONIC AND ELECTROCHEMICAL PROPERTIES OF POLY(ISOTHIANAPHTHENE) [J].

KOBAYASHI, M ;

COLANERI, N ;

BOYSEL, M ;

WUDL, F ;

HEEGER, AJ .

JOURNAL OF CHEMICAL PHYSICS, 1985, 82 (12) :5717-5723