FORMATION OF BICYCLO[2.2.0]HEXANE DERIVATIVES BY THE RING CONTRACTION OF BICYCLO[3.2.0]HEPTANONES

被引：29

作者：

WIBERG, KB

FURTEK, BL

OLLI, LK

机构：

[1] Department of Chemistry, Yale University, New Haven, Connecticut

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 26期

关键词：

D O I：

10.1021/ja00520a008

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring contraction via the photochemical Wolff rearrangement of diazo ketones has been applied to several cis-bicy-clo[3.2.0]heptan-2-and-3-ones to give substituted cis-bicyclo[2.2.0]hexanes. The ring contraction was unsuccessful with trans-bicyclo[3.2.0]heptan-3-one. The diazo ketone was unstable and in methanol gave methyl cyclopent-2-en-1-acetate. © 1979, American Chemical Society. All rights reserved.

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页码：7675 / 7679

页数：5

相关论文

共 30 条

[1] THE RELATIVE STABILITIES OF CIS AND TRANS ISOMERS .5. THE BICYCLO[5.2.0]NONANES - AN EXTENSION OF THE CONFORMATIONAL RULE [J].

ALLINGER, NL ;

NAKAZAKI, M ;

ZALKOW, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (15) :4074-4080

[2] A CONVENIENT SYNTHESIS OF CUBANE SYSTEM [J].

BARBORAK, JC ;

WATTS, L ;

PETTIT, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (06) :1328-&

[3]

BLOOMFIELD JJ, 1972, J AM CHEM SOC, V93, P782

[4] ACID AMIDE-REACTIONS L - ORTHO-AMIDES .I. SYNTHESIS AND PROPERTIES OF AMIDE ACETALES AND AMINALESTERS [J].

BREDERECK, H ;

SIMCHEN, G ;

REBSDAT, S ;

KANTLEHNER, W ;

HORN, P ;

WAHL, R ;

HOFFMANN, H ;

GRIESHABER, P .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (01) :41-+

[5] NEW SYNTHESIS OF CYCLOPENTENONES - METHYL JASMONATE AND JASMONE [J].

BUCHI, G ;

EGGER, B .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (14) :2021-&

[6] CATALYSIS OF SYMMETRY-RESTRICTED REACTIONS BY TRANSITION METAL COMPOUNDS - VALENCE ISOMERIZATION OF CUBANE [J].

CASSAR, L ;

EATON, PE ;

HALPERN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (11) :3515-&

[7] PHOTOCHEMICAL TRANSFORMATIONS OF CONJUGATED CYCLOHEPTADIENES [J].

CHAPMAN, OL ;

PASTO, DJ ;

GRISWOLD, AA ;

BORDEN, GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (07) :1220-&

[8]

CONIA JM, 1968, B SOC CHIM FR, P3327

[9] [2.2.2]PROPELLANE SYSTEM [J].

EATON, PE ;

TEMME, GH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7508-7510

[10] PHOTOCHEMICAL REACTIONS OF SIMPLE ALICYCLIC ENONES [J].

EATON, PE .

ACCOUNTS OF CHEMICAL RESEARCH, 1968, 1 (02) :50-&