ELECTROCHEMICAL CYCLODIMERIZATION OF ALKYLIDENEMALONATES

被引:15
作者
ELINSON, MN [1 ]
FEDUCOVICH, SK [1 ]
ZAKHARENKOV, AA [1 ]
UGRAK, BI [1 ]
NIKISHIN, GI [1 ]
LINDEMAN, SV [1 ]
STRUCHKOV, JT [1 ]
机构
[1] RUSSIAN ACAD SCI, AN NESMEYANOV ORGANOELEMENT CPDS INST, MOSCOW, RUSSIA
关键词
D O I
10.1016/0040-4020(95)98700-R
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electrolysis of dimethyl alkylidenemalonates RCH=C(COOMe)(2) (R=n-Alk, Ph) in an undivided cell in MeOH in the presence of alkali metal halide as mediator, leads to the formation of cyclic dimers, i.e., 3,4-disubstituted 1,1,2,2-cyclobutanetetracarboxylates. The reaction proceeds via the reductive coupling of two substrate molecules at cathode and the cyclization of a hydrodimer dianion by its interaction with an active form of a mediator, an anode-generated halogen.
引用
收藏
页码:5035 / 5046
页数:12
相关论文
共 19 条
[1]  
White, Dunathan, J. Am. Chem. Soc., 78, pp. 6055-6057, (1956)
[2]  
Griffin, Basinsky, Vellturo, Tetrahedron Lett., 1, pp. 13-16, (1960)
[3]  
Griffin, Basinsky, Peterson, J. Am. Chem. Soc., 84, pp. 1012-1015, (1962)
[4]  
Cohen, Schmidt, Sonntag, 384. Topochemistry. Part II. The photochemistry of trans-cinnamic acids, Journal of the Chemical Society (Resumed), pp. 2000-2013, (1964)
[5]  
Delaunay, Mabon, Orliac, Simonet, Tetrahedron Lett., 31, (1990)
[6]  
Schafer, Anodic and Cathodic CC-Bond Formation, Angewandte Chemie International Edition in English, 20, pp. 911-933, (1981)
[7]  
Vogel, CCLX.?Syntheses of cyclic compounds. Part I. Ethyl ??-dimethylbutane-????-tetracarboxylate and some cyclobutane compounds derived therefrom, Journal of the Chemical Society (Resumed), pp. 1985-1994, (1927)
[8]  
Bacher, Studien zur Truxin- und Truxills�uresynthese, Journal f�r Praktische Chemie, 120, pp. 328-338, (1928)
[9]  
Perkin, I.?The synthetical formation of closed carbon-chains. Part II. On some derivatives of tetramethylene, Journal of the Chemical Society, Transactions, pp. 1-28, (1887)
[10]  
White, Syntheses with Electrogenerated Halogens, Journal of The Electrochemical Society, 124, pp. 1177-1184, (1977)