Electrochemical carboxylation of bicyclo[n.1.0]alkylidene derivatives

被引:27
作者
Chowdhury, MA [1 ]
Senboku, H [1 ]
Tokuda, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Organ Synth Lab, Sapporo, Hokkaido 0608628, Japan
基金
日本学术振兴会;
关键词
electrochemical carboxylation; bicyclo[n.1.0]alkylidene derivative; ring-fused alkylidenecyclopropane; carbon dioxide; carboxylic acid;
D O I
10.1016/j.tet.2003.10.126
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electrochemical carboxylation of bicyclo[n.1.0]alkylidene derivatives (ring-fused alkylidenecyclopropanes) in a suitable aprotic solvent using a one-compartment electrochemical cell equipped with a platinum plate cathode and a zinc plate anode under an atmospheric pressure of carbon dioxide afforded either mono- or dicarboxylic acid in moderate to good yields. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:475 / 481
页数:7
相关论文
共 40 条
[1]   UPPER EXCITED STATE(S) IN THE METHYLENECYCLOPROPANE TRIMETHYLENEMETHANE SYSTEM - PHOTOLYSIS OF (E) AND (Z)-2,3-DIETHYL-2-METHYLMETHYLENECYCLOPROPANE AT 185 NM [J].
BAUM, T ;
ROSSI, A ;
SRINIVASAN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4411-4415
[2]   Synthesis of mono-, di-, and trisilyl-substituted alkenes via the hydrosilylation of methylenecyclopropanes catalyzed by Rh(I) complexes [J].
Bessmertnykh, AG ;
Blinov, KA ;
Grishin, YK ;
Donskaya, NA ;
Tveritinova, EV ;
Yureva, NM ;
Beletskaya, IP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6069-6076
[3]   REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .8. SELECTIVE FORMATION OF TETRAHYDROPYRIDONES FROM C,C-DISUBSTITUTED NITRONES [J].
BRANDI, A ;
DURUST, Y ;
CORDERO, FM ;
DESARLO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5666-5670
[4]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269
[5]  
Camacho DH, 1999, ANGEW CHEM INT EDIT, V38, P3365, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3365::AID-ANIE3365>3.0.CO
[6]  
2-5
[7]   Palladium-catalyzed addition of alcohol pronucleophiles to alkylidenecyclopropanes [J].
Camacho, DH ;
Nakamura, I ;
Saito, S ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :270-275
[8]   ME3SICN .7. PALLADIUM-CATALYZED AND NICKEL-CATALYZED REACTION OF METHYLENECYCLOPROPANES WITH TRIMETHYLSILYL CYANIDE [J].
CHATANI, N ;
TAKEYASU, T ;
HANAFUSA, T .
TETRAHEDRON LETTERS, 1988, 29 (32) :3979-3982
[9]  
CHAUSSARD J, 1990, SYNTHESIS-STUTTGART, P369
[10]   A new synthesis of ring-fused alkylidenecyclobutanes by ring-enlargement reaction of bicyclo[n.1.0]alkylidene derivatives [J].
Chowdhury, MA ;
Senboku, H ;
Tokuda, M .
TETRAHEDRON LETTERS, 2003, 44 (16) :3329-3332