THE DECOMPOSITION OF CIS-FUSED CYCLOPENTENO-1,2,4-TRIOXANES INDUCED BY FERROUS SALTS AND SOME OXOPHILIC REAGENTS

被引：71

作者：

JEFFORD, CW

FAVARGER, F

VICENTE, MDGH

JACQUIER, Y

机构：

[1] Department of Organic Chemistry, University of Geneva, Geneva

来源：

HELVETICA CHIMICA ACTA | 1995年 / 78卷 / 02期

关键词：

D O I：

10.1002/hlca.19950780216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two cis-fused cyclopenteno-1,2,4-trioxanes, 1a and 1b, were subjected to Zn in AcOH or FeCl2 4H(2)O in MeCN. In the first case, the main course was deoxygenation to give cyclopentanone (18) and the 1,4-diphenyl- or 1,4-bis(4-fluorophenyl)cyclopent-3-ene-1,2-diol 10 (Scheme 5). In the second case, isomerization chiefly occurred resulting in the formation of a dimer 9 of the respective 3,5-diaryl-5-hydroxycyclopent-2-enyl 5-hydroxypentanoates 8 (Scheme 3).

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页码：452 / 458

页数：7

相关论文

共 18 条

[1] IRON(O) OXIDATION BY HYDROGEN-CHLORIDE IN TETRAHYDROFURAN - SIMPLE WAY TO ANHYDROUS IRON(II) CHLORIDE [J].

ARESTA, M ;

NOBILE, CF ;

PETRUZZELLI, D .

INORGANIC CHEMISTRY, 1977, 16 (07) :1817-1818

[2] Some 1,4-diaryl-1,3-cyclopentadienes [J].

Drake, NL ;

Adams, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1939, 61 :1326-1329

[3]

DRENTH J, 1980, RECL TRAV CHIM PAY B, V99, P185

[4] IS CONCERTED ENE MECHANISM OF DELTA-1(G) EXCITED OXYGEN MOLECULE REACTIONS WITH OLEFINS REALLY ELIMINATED - PHOTOOXYGENATION AND ELECTROLYSIS IN PRESENCE OF AZIDE IONS [J].

GOLLNICK, K ;

SCHADE, G ;

HAISCH, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (05) :1747-&

[5] THIOUREA, A CONVENIENT REAGENT FOR THE REDUCTIVE CLEAVAGE OF OLEF IN OZONOLYSIS PRODUCTS [J].

GUPTA, D ;

SOMAN, R ;

DEV, S .

TETRAHEDRON, 1982, 38 (20) :3013-3018

[6]

JEFFORD CW, 1989, HETEROCYCLES, V28, P673

[7]

JEFFORD CW, 1984, J CHEM SOC CHEM COMM, P523, DOI 10.1039/c39840000523

[8] REACTION OF BICYCLIC ENDOPEROXIDES WITH CARBONYL-COMPOUNDS - A NEW APPROACH TO 1,2,4-TRIOXANES [J].

JEFFORD, CW ;

JAGGI, D ;

BOUKOUVALAS, J ;

KOHMOTO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (21) :6497-6498

[9]

JEFFORD CW, 1993, PERSPECTIVES MED CHE, pCH29

[10] IRON-DEPENDENT FREE-RADICAL GENERATION FROM THE ANTIMALARIAL AGENT ARTEMISININ (QINGHAOSU) [J].

MESHNICK, SR ;

YANG, YZ ;

LIMA, V ;

KUYPERS, F ;

KAMCHONWONGPAISAN, S ;

YUTHAVONG, Y .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1993, 37 (05) :1108-1114