Synthesis of annulenes via multiple wittig reactions;: In-situ dimerization of 1,2;5,6-dibenzocyclooctatetraene

被引：4

作者：

Bornhoeft, Jan ^{[1
]}

Siegwarth, Jan ^{[1
]}

Naether, Christian ^{[2
]}

Herges, Rainer ^{[1
]}

机构：

[1] Univ Kiel, Otto Diels Inst Organ Chem, D-24098 Kiel, Germany

[2] Univ Kiel, Inst Anorgan Chem, D-24098 Kiel, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 09期

关键词：

wittig reaction; dimerization; annulenes; hydrogenation; macrocycles;

D O I：

10.1002/ejoc.200701174

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple synthetic route to tetrabenzo[16]- and hexabenzo-[24]annulene systems using one-pot multiple Wittig reactions is presented. We report the characterization of the all-trans-isomer of tetrabenzo[16]annulene by NMR spectroscopy and X-ray diffraction. Several isomers of an unexpected, tetra-benzocyclooctatetraene dimer product are also isolated and identified by NMR- and X-ray diffraction studies.

引用

页码：1619 / 1624

页数：6

共 33 条

[1] STEPWISE CATHODIC REDUCTION OF [24] PARACYCLOPHANETETRAENE [J].

ANKNER, K ;

LAMM, B ;

THULIN, B ;

WENNERSTROM, O .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (06) :391-394

[2] SYNTHESES OF MACROCYCLIC COMPOUNDS [J].

BERGMANN, ED ;

PELCHOWICZ, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (17) :4281-4286

[3]

Block E., 1984, Org. React, V30, P457, DOI DOI 10.1002/0471264180.OR030.02

[4] OCTALENE DERIVATIVES [J].

BRESLOW, R ;

HORSPOOL, W ;

SUGIYAMA, H ;

VITALE, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (15) :3677-&

[5]

Chaffins S, 2002, SYNTHESIS-STUTTGART, P1191

[6]

Ciorba V., 1987, ANNULENES BENZO HETE, VI

[7] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS [J].

COREY, EJ ;

WINTER, RAE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) :2677-&

[8] THE MOLECULAR-STRUCTURE OF 6, 8, 6 AND RELATED SYSTEMS [J].

DOMIANO, P ;

COZZINI, P ;

CLARAMUNT, RM ;

LAVANDERA, JL ;

SANZ, D ;

ELGUERO, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (09) :1609-1620

[9] INTERMOLECULAR PINACOL CROSS COUPLING OF ELECTRONICALLY SIMILAR ALDEHYDES - AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF 1,2-DIOLS EMPLOYING A PRACTICAL VANADIUM(II) REAGENT [J].

FREUDENBERGER, JH ;

KONRADI, AW ;

PEDERSEN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8014-8016

[10]

GHELARDONI MARIO, 1962, ANN CHIM, V52, P29

← 1 2 3 4 →