HIGHLY DISTORTED CONE CALIX[4]ARENES THROUGH INTRAMOLECULAR MCMURRY COUPLING REACTION

被引:29
作者
ARDUINI, A
FANNI, S
POCHINI, A
SICURI, AR
UNGARO, R
机构
[1] Dipartimemo di Chimica Organica, Industriale dell'Università, 43100 Parma, Viale delle Scienze
关键词
D O I
10.1016/0040-4020(95)00411-Z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly distorted and rigid cone conformers of calix[4]arene have been synthesized by low-valent titanium promoted intra-molecular coupling of aldehydes 1a-d. The reaction outcome strongly depends on the substituents present at the upper rim and reaction time. In all cases examined intramolecular coupled compounds, having a bridge only two atoms long, were obtained in about 30% yield.
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页码:7951 / 7958
页数:8
相关论文
共 18 条
[1]  
Andreetti G.D., 1991, INCLUSION COMPOUNDS, V4, P64
[2]   GAS-PHASE COMPLEXATION OF NEUTRAL MOLECULES BY UPPER RIM BRIDGED CALIX[4]ARENES [J].
ARDUINI, A ;
CANTONI, M ;
GRAVIANI, E ;
POCHINI, A ;
SECCHI, A ;
SICURI, AR ;
UNGARO, R ;
VINCENTI, M .
TETRAHEDRON, 1995, 51 (02) :599-606
[3]   DIRECT REGIOSELECTIVE FORMYLATION OF TETRAALKOXYCALIX[4]ARENES FIXED IN THE CONE CONFORMATION AND SYNTHESIS OF NEW CAVITANDS [J].
ARDUINI, A ;
FANNI, S ;
MANFREDI, G ;
POCHINI, A ;
UNGARO, R ;
SICURI, AR ;
UGOZZOLI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1448-1453
[4]  
ARUBINI A, 1995, J ORG CHEM, V60, P1454
[5]   REDUCTIVE COUPLING OF AROMATIC KETONES BY LOW-VALENT TITANIUM SALTS [J].
BOTTINO, FA ;
FINOCCHIARO, P ;
LIBERTINI, E ;
REALE, A ;
RECCA, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (01) :77-81
[6]   NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].
COREY, EJ ;
DANHEISER, RL ;
CHANDRASEKARAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265
[7]   A SERIES OF CALIX[4]ARENES, HAVING 2 OPPOSITE PARA POSITIONS CONNECTED BY AN ALIPHATIC CHAIN [J].
GOLDMANN, H ;
VOGT, W ;
PAULUS, E ;
BOHMER, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6811-6817
[8]   COMPUTATIONAL STUDY OF THE STRUCTURAL, ENERGETICAL, AND ACID-BASE PROPERTIES OF CALIX[4]ARENES [J].
GROOTENHUIS, PDJ ;
KOLLMAN, PA ;
GROENEN, LC ;
REINHOUDT, DN ;
VANHUMMEL, GJ ;
UGOZZOLI, F ;
ANDREETTI, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4165-4176
[9]  
Gutsche C. D., 1989, CALIXARENES
[10]   COMPUTATIONAL STUDIES OF CALIX[4]ARENE HOMOLOGS - INFLUENCE OF 5,11,17,23-SUBSTITUENTS AND 25,26,27,28-SUBSTITUENTS ON THE RELATIVE STABILITY OF 4 CONFORMERS [J].
HARADA, T ;
RUDZINSKI, JM ;
OSAWA, E ;
SHINKAI, S .
TETRAHEDRON, 1993, 49 (27) :5941-5954