SYNTHESIS, CHEMICAL TRAPPING, AND DIMERIZATION OF 3,7-DIMETHYLTRICYCLO[3.3.0.0(3,7)]OCT-1(5)-ENE - [2+2]-RETROCYCLOADDITION OF THE CYCLOBUTANE DIMER

被引:43
作者
CAMPS, P [1 ]
FONTBARDIA, M [1 ]
PEREZ, F [1 ]
SOLANS, X [1 ]
VAZQUEZ, S [1 ]
机构
[1] UNIV BARCELONA,SERV CIENTIFICO TECN,BARCELONA,SPAIN
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 08期
关键词
ALKENES; CAGE; COMPOUNDS; DIELS-ALDER REACTIONS; HYDROCARBONS;
D O I
10.1002/anie.199509121
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reduction of 1 with sodium or tert‐butyllithium yields the diene dimer 3. The key intermediate, the strongly pyramidalized alkene 2, dimerizes to give a cyclobutane dimer, which then leads to 3. Compound 2 can also be trapped as a Diels‐Alder adduct with 1,3‐dienes. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
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页码:912 / 914
页数:3
相关论文
共 37 条
[1]   PYRAMIDALIZED ALKENES [J].
BORDEN, WT .
CHEMICAL REVIEWS, 1989, 89 (05) :1095-1109
[2]   GENERATION AND CHEMICAL TRAPPING OF A BIS(ETHANO) DERIVATIVE OF TRICYCLO[3.3.0.0[3,7]]OCT-1(5)-ENE - THE CONSUMMATE MEMBER OF A SERIES OF PYRAMIDALIZED ALKENES [J].
BRANAN, BM ;
PAQUETTE, LA ;
HROVAT, DA ;
BORDEN, WT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :774-776
[3]   STEREOSELECTIVE SYNTHESIS OF DIMETHYL TETRACYCLO(5.2.1.02,6.03,8)DECANE-7,8-DICARBOXYLATE [J].
CAMPS, P ;
CASTANE, J ;
SANTOS, MT .
CHEMISTRY LETTERS, 1984, (08) :1367-1370
[4]   A SHORT SYNTHESIS OF DIMETHYL TRICYCLO[3.3.0.0/3,7]OCTANE-1,5-DICARBOXYLATE AND ITS 3,7-DIMETHYL DERIVATIVE - A NEW ROUTE TO THE TRICYCLO[3.3.0.0/3,7]OCTANE SKELETON [J].
CAMPS, P ;
IGLESIAS, C ;
RODRIGUEZ, MJ ;
GRANCHA, MD ;
GREGORI, ME ;
LOZANO, R ;
MIRANDA, MA ;
FIGUEREDO, M ;
LINARES, A .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (04) :647-654
[5]   TRICYCLO[3.2.2.02,4]NON-2(4)-ENE - SYNTHESIS AND TRAPPING OF A STRAINED CYCLOPROPENE [J].
CHENIER, PJ ;
SOUTHARD, DA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4333-4337
[6]   SYNTHESIS AND CHEMISTRY OF SOME TRICYCLIC CYCLOPROPENES .3. TRICYCLO[3.2.1.0(2,4)]OCT-2(4)-ENE [J].
CHENIER, PJ ;
BAUER, MJ ;
HODGE, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5959-5962
[7]   IODOSOBENZENE DIACETATE, AN EFFICIENT REAGENT FOR THE OXIDATIVE DECARBOXYLATION OF CARBOXYLIC-ACIDS [J].
CONCEPCION, JI ;
FRANCISCO, CG ;
FREIRE, R ;
HERNANDEZ, R ;
SALAZAR, JA ;
SUAREZ, E .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (03) :402-404
[8]  
Eaton P. E., 1992, ANGEW CHEM, V104, P1447
[9]   CUBANES - STARTING MATERIALS FOR THE CHEMISTRY OF THE 1990S AND THE NEW CENTURY [J].
EATON, PE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (11) :1421-1436
[10]   SYNTHESIS, TRAPPING, AND DIMERIZATION OF 9,10-BENZOTRICYCLO[3.3.2.03,7]DECA-3(7),9(10)-DIENE - X-RAY CRYSTAL-STRUCTURE OF DIMER [J].
GREENHOUSE, R ;
BORDEN, WT ;
HIROTSU, K ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1664-1666