Synthesis of the syn and anti isomer of 1,4,5,8,9,12-hexahydro-2,3,6,7,10,11-hexamethylidene-1,4:5,8:9,12-trimethanotriphenylene and Diels-Alder reactivity of the syn isomer

被引：21

作者：

Borsato, G

De Lucchi, O

Fabris, F

Lucchini, V

Pasqualotti, M

Zambon, A

机构：

[1] Univ Ca Foscari Venezia, Dipartimento Sci Ambientali, I-30123 Venice, Italy

[2] Univ Ca Foscari Venezia, Dipartmento Chim, I-30123 Venice, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 03期

关键词：

D O I：

10.1016/S0040-4039(02)02533-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compounds, new members in the class of tris-annelated benzenes with [2.2.1] bicyclic rings, were obtained in high yields by coupling of 2-bromo-3-trimethyltin-5,6-dimethylenenorborn-2-ene with copper(l) 2-thiophenecarboxylate (CuTC). The syn isomer was reacted with 3 equiv. of the dienophiles TCNE, DMAD, PTAD and norbornadiene to afford the corresponding cycloadducts. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：561 / 563

页数：3

相关论文

共 18 条

[11] The cyclotrimerisation of (+)-camphor [J].

Fabris, F ;

De Martin, A ;

De Lucchi, O .

TETRAHEDRON LETTERS, 1999, 40 (51) :9121-9124

[12] INTERACTION BETWEEN NON-CONJUGATED CHROMOPHORES .17. EFFECTS OF REMOTE SUBSTITUTION ON THE PHOTOOXIDATION OF EXOCYCLIC S-CIS-BUTADIENES GRAFTED ONTO BICYCLO[2.2.1]HEPTANES - THERMAL AND RHODIUM CATALYZED REARRANGEMENTS OF 3,6-DIHYDRO-1,2-DIOXINES [J].

HAGENBUCH, JP ;

BIRBAUM, JL ;

METRAL, JL ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1982, 65 (03) :887-895

[13] Palladium-catalysed cyclotrimerisation reactions of polycyclic alkenes under the Stille and Grigg coupling conditions [J].

Paulon, A ;

Cossu, S ;

De Lucchi, O ;

Zonta, C .

CHEMICAL COMMUNICATIONS, 2000, (19) :1837-1838

[14] SIMPLE PREPARATION OF 2,3-DIMETHYLENEBICYCLO[2.2.1]HEPT-5-ENE [J].

TODA, T ;

MUKAI, T ;

OHYA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (05) :1561-+

[15] STUDIES OF BENZONORBORNENE AND DERIVATIVES .2. AC-BROMOBENZONORBORNENES AND AC-BROMOBENZONORBORNADIENES [J].

WILT, JW ;

CHENIER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) :1562-&

[16] Ambient temperature, Ullmann-like reductive coupling of aryl, heteroaryl, and alkenyl halides [J].

Zhang, SJ ;

Zhang, DW ;

Liebeskind, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2312-2313

[17]

Zonta C, 2000, EUR J ORG CHEM, V2000, P1965

[18] Stereochemistry of the cyclotrimerisation of enantiopure polycyclic bromostannylalkenes: Mechanistic considerations on the coupling of alkenyl stannanes by copper(II) nitrate [J].

Zonta, C ;

Cossu, S ;

Peluso, P ;

De Lucchi, O .

TETRAHEDRON LETTERS, 1999, 40 (46) :8185-8188