Synthesis, chemical trapping and dimerization of tricyclo[3.3.0.0(3,7)]oct-1(5)-ene, the consummate member of a series of pyramidalized alkenes

被引：32

作者：

Camps, P

Luque, FJ

Orozco, M

Perez, F

Vazquez, S

机构：

[1] UNIV BARCELONA,FAC FARM,UNITAT FIS QUIM,E-08028 BARCELONA,SPAIN

[2] UNIV BARCELONA,FAC FARM,DEPT BIOQUIM,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 47期

关键词：

D O I：

10.1016/0040-4039(96)01967-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of tricyclo[3.3.0.0(3,7)]oct-1(5)-ene, 5, the consummate member of a series of pyramidalized alkenes, has been carried out by deiodination of 4 in different ways. Reaction of 4 with sodium in boiling dioxane gave in good yield diene 8, whose formation can be easily explained through the intermediacy of 5 and its cyclobutane dimer 6. Reaction of 4 with t-butyllithium in THF at -78 degrees C in the presence of 1,3-diphenylisobenzofurane gave 10, a Diels-Alder adduct derived from 5. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：8605 / 8608

页数：4

相关论文

共 13 条

[1] SELF-CONSISTENT MOLECULAR-ORBITAL METHODS .21. SMALL SPLIT-VALENCE BASIS-SETS FOR 1ST-ROW ELEMENTS [J].

BINKLEY, JS ;

POPLE, JA ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :939-947

[2]

Borden WT, 1996, SYNLETT, P711

[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] PREPARATION OF DIMETHYL 7-OXOBICYCLO[2.2.1]HEPTANE-EXO-2,EXO-3-DICARBOXYLATE - AN EASY ROUTE TO FUNCTIONALIZED NORBORNANE DERIVATIVES AND CAGE COMPOUNDS [J].

CAMPS, P ;

MAULEON, D ;

MINGUILLON, C ;

PARCERISA, X ;

PEREZ, F .

CHEMISCHE BERICHTE-RECUEIL, 1990, 123 (08) :1715-1718

[5] 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

[6] A NEW SYNTHETIC ENTRY INTO THE TRICYCLO (3.3.0.03,7) OCTANE SKELETON [J].

CAMPS, P ;

IGLESIAS, C ;

LOZANO, R ;

MIRANDA, MA ;

RODRIGUEZ, MJ .

TETRAHEDRON LETTERS, 1987, 28 (16) :1831-1832

[7]

Camps P., 1995, ANGEW CHEM, V107, P1011

[8] 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

[9]

FRISCH MJ, 1995, GAUSSIAN 94 REV A 1

[10] INFLUENCE OF POLARIZATION FUNCTIONS ON MOLECULAR-ORBITAL HYDROGENATION ENERGIES [J].

HARIHARA.PC ;

POPLE, JA .

THEORETICA CHIMICA ACTA, 1973, 28 (03) :213-222