Synthesis and reaction of 1,4-acetal-bridged 2,3,5,6-tetramethylidene-bicyclo[2.2.0]hexane: the first Diels-Alder route to Dewar benzenes

被引：1

作者：

Ohkita, M ^{[1
]}

Suzuki, T ^{[1
]}

Tsuji, T ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 19期

关键词：

D O I：

10.1039/a906239d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1,4-acetal-bridged derivative of hitherto unknown 2,3,5,6-tetramethylidenebicyclo[2.2.0]hexane, which produces the Dewar benzene skeleton through two successive Diels-Alder reactions with dienophiles, has been synthesized in four steps from dimethyl acetylenedicarboxylate and 1,4-dichlorobut-2-ene.

引用

页码：1999 / 2000

页数：2

共 15 条

[1]

BICKELHAUPT F, 1988, RECL TRAV CHIM PAY B, V107, P459

[2]

Bickelhaupt F., 1993, Advances in Strain in Organic Chemistry, V3, P185

[3] MOLECULAR LADDERS CONSTITUTED OF LATERALLY-FUSED 1,4-CYCLOHEXADIENE SUBUNITS - OPEN-CHAIN MODELS OF THE [N]BELTENES [J].

GRAHAM, RJ ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5770-5777

[4]

Greenberg A., 1978, STRAINED ORGANIC MOL

[5] SYNTHESIS OF SMALL CYCLOPHANES [J].

KANE, VV ;

DEWOLF, WH ;

BICKELHAUPT, F .

TETRAHEDRON, 1994, 50 (16) :4575-4622

[6] IS 2,3,5,6-TETRAKIS(METHYLENE)BICYCLO[2.2.0]HEXANE THE PRODUCT OF PHOTOLYZING 7-OXA[2.2.1]HERICENE [J].

LIU, RF ;

ZHOU, XF ;

HINTON, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6925-6926

[7]

MCDONALD RN, 1972, J ORG CHEM, V37, P1704

[8] SYNTHESIS AND DIELS-ALDER REACTIVITY OF 2,3,5,6-TETRAMETHYLIDENENORBORNANE [J].

PILET, O ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1981, 64 (08) :2563-2570

[9] 9,10-DEWAR-ANTHRACENE [J].

PRITSCHINS, W ;

GRIMME, W .

TETRAHEDRON LETTERS, 1982, 23 (11) :1151-1154

[10] A KINETICALLY STABLE SINGLET-STATE OF 1,2,4,5-TETRAMETHYLENEBENZENE [J].

REYNOLDS, JH ;

BERSON, JA ;

KUMASHIRO, KK ;

DUCHAMP, JC ;

ZILM, KW ;

RUBELLO, A ;

VOGEL, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :763-764

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