NITROCYCLOPROPANES FROM NITRODIAZOMETHANES - PREPARATION AND REACTIVITY

被引：85
作者：
OBANNON, PE [1 ]
DAILEY, WP [1 ]
机构：
[1] UNIV PENN, DEPT CHEM, PHILADELPHIA, PA 19104 USA
来源：
TETRAHEDRON | 1990年 / 46卷 / 21期
关键词：
D O I：
10.1016/S0040-4020(01)89052-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nitrodiazo compounds cyclopropanate electron rich alkenes in the presence of rhodium(II) acetate. The yields and diastereoselectivities are dependent on both the alkene and the nitrodiazo precursor. Nitrocyclopropanecarboxylates undergo ring opening, reduction and hydrolysis. © 1990.
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页码：7341 / 7358
页数：18
相关论文
共 70 条
[1]   TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .1. CYCLOPROPANATION OF DOUBLE-BONDS [J].
ANCIAUX, AJ ;
HUBERT, AJ ;
NOELS, AF ;
PETINIOT, N ;
TEYSSIE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (04) :695-702
[2]   SYNTHESIS OF POLYNITROADAMANTANES - OXIDATIONS OF OXIMINOADAMANTANES [J].
ARCHIBALD, TG ;
BAUM, K .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4645-4649
[3]   DIAZOACETALDEHYDE AS A SOURCE OF FORMYLCARBENE - A NEW CARBENE SPECIES [J].
ARNOLD, Z .
CHEMICAL COMMUNICATIONS, 1967, (06) :299-&
[4]  
ASUNSKIS J, 1961, J ORG CHEM, V26, P1831
[5]  
BALLI H, 1966, TETRAHEDRON LETT, P5821
[6]   DIAZO-GROUP TRANSFER TO ACTIVE METHYLENE-COMPOUNDS USING AZIDINIUM SALTS [J].
BALLI, H ;
LOW, R ;
MULLER, V ;
REMPFLER, H ;
SEZENGEZGIN, A .
HELVETICA CHIMICA ACTA, 1978, 61 (01) :97-103
[7]  
BRIDSON JN, 1988, ORG SYNTH, V50-9, P386
[8]   ASYMMETRICAL CATALYSTS .21. ENANTIOSELECTIVE CYCLOPROPANATION OF 1,1-DIPHENYLETHYLENE AND DIAZOACETIC ACID ESTER WITH COPPER-CATALYSTS [J].
BRUNNER, H ;
MIEHLING, W .
MONATSHEFTE FUR CHEMIE, 1984, 115 (10) :1237-1254
[9]  
CACCHI S, 1980, SYNTHESIS-STUTTGART, P243
[10]   STUDIES IN STEREOCHEMISTRY .46. SINGLET DIRADICAL TRANSITION-STATES IN EPIMERIZATION REACTIONS OF SUBSTITUTED CYCLOPROPANES [J].
CHMURNY, AB ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (13) :4237-4244
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