BICYCLO[4.2.0]OCT-3-ENE-7,8-DIONE AND ITS MONOENOL SILYL ETHER

被引：10

作者：

CARPINO, LA

TSAO, JH

机构：

[1] Department of Chemistry, University of Massachusetts, Massachusetts

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 14期

关键词：

D O I：

10.1021/jo01328a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The readily available enediol bis(trimethylsilyl) ether 7 has been demonstrated to be a useful intermediate in the synthesis of free bicyclo[4.2.0]oct-3-ene-7, 8-dione (3) as well as a protected form, the monoenol silyl ether 6. Bromination of 7 gave small amounts of both 3 and 6. If bromination was followed by addition of triethyl amine, 6 could be obtained in 41% yield. Other products isolated from the bromination of 7, depending on the conditions, were the cyclobutene-1, 2-dione 13, the benzocyclobutene-l, 2-dione 15, and the benzocyclobutenol silyl ether 16. The best route to 3 involved the oxidative desilylation of 7 by means of DDQ in dioxane. © 1979, American Chemical Society. All rights reserved.

引用

收藏

页码：2387 / 2391

页数：5

相关论文

共 34 条

[1] 1,2-CYCLOBUTANEDIONES .2. SPECTRAL CHARACTERISTICS OF [4.4.2]PROPELLA-3,8-DIENE-11,12-DIONE AND ITS DI- AND TETRAHYDRO DERIVATIVES [J].

BLOOMFIE.JJ ;

MOSER, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5625-&

[2]

BLOOMFIELD JJ, 1968, TETRAHEDRON LETT, P5647

[3]

BLOOMFIELD JJ, 1968, TETRAHEDRON LETT, P587

[4]

BOGERT MT, 1941, ORG SYNTH, V1, P220

[5] FORMATION OF ENDO-2-PHENYLTHIO-EXO-3-CHLORO-7,7-DIMETHYLNORBORNANE FROM ADDITION OF BENZENESULFENYL CHLORIDE TO 7,7-DIMETHYLNORBORNEN - FURTHER EVIDENCE FOR DOMINANT STERIC CONTROL BY 7,7-DIMETHYL SUBSTITUENTS ON DIRECTION ADDITIONS TO NORBORNENE MOIETY [J].

BROWN, HC ;

LIU, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (11) :3502-&

[6] ADDITIONS TO BICYCLIC OLEFINS .5. EFFECT OF 7,7-DIMETHYL SUBSTITUENTS ON STEREOCHEMISTRY AND RATES OF CYCLIC ADDITIONS TO NORBORNENES [J].

BROWN, HC ;

KAWAKAMI, JH ;

LIU, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2209-2216

[7] ACTION OF NUCLEOPHILES ON 8-TOSYLOXY-CIS-BICYCLO(4.2.0)OCTAN-7-TRANS-ONE - SPECTROSCOPIC DETERMINATION OF A BICYCLO(4.1.0)HEPTANIC DERIVATIVE WITH A TRANS RING JUNCTION [J].

CASADEVALL, E ;

POUET, Y .

TETRAHEDRON, 1978, 34 (13) :1921-1930

[8] CYCLE CONTRACTION STARTING WITH CIS 8-ENDO TOSYLOXYBICYCLO[4.2.0]OCT-3-EN-7-ONE [J].

CASADEVALL, E ;

POUET, Y .

TETRAHEDRON, 1975, 31 (07) :757-763

[9] CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .26. BENZOCYCLOBUTADIENOQUINONE - SYNTHESIS AND SIMPLE TRANSFORMATIONS [J].

CAVA, MP ;

POHL, RJ ;

NAPIER, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2076-&

[10] LITHIUM ENOLATE OF CYCLO-OCTA-2,4,6-TRIENONE AND ITS REACTIONS WITH ELECTROPHILES [J].

CHALONER, PA ;

HOLMES, AB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (17) :1838-1842

← 1 2 3 4 →