The spirodienone route for the functionalization of calixarenes

被引:36
作者
Biali, SE [1 ]
机构
[1] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel
关键词
calixarenes; macrocycles; spirodienone; synthesis; carbonyl;
D O I
10.1055/s-2003-36212
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mild oxidation of calixarenes affords their spirodienone derivatives. These derivatives are useful synthetic intermediates for the selective functionalization of calixarenes. The presence of several functionalities (carbonyl, ether, diene) within the calix scaffold enables them to undergo a large number of synthetic transformations. The spirodienone calixarene derivatives have been utilized for the selective derivatization of two vicinal OH groups, the replacement of one or two OH groups, the formation of Ar-O-Ar bonds between neighboring aryl groups, the functionalization of the calix scaffold at the extraannular positions (via spirodienol derivatives), and the modification of the methylene groups.
引用
收藏
页码:1 / 11
页数:11
相关论文
共 82 条
[1]  
Abel J., 1892, BER, V25, P3477
[2]   Spirodienone route for the stereoselective methylene functionalization of p-tert-butylcalix[4]arene [J].
Agbaria, K ;
Biali, SE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12495-12503
[3]   Extraannular fluorinated calixarenes:: Regiospecificity of the deoxofluorination reactions of bis(spirodienol) derivatives [J].
Agbaria, K ;
Wöhnert, J ;
Biali, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :7059-7066
[4]   Intramolecular Ar-O-Ar bond formation in calixarenes [J].
Agbaria, K ;
Biali, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5482-5489
[5]   Stereochemistry of a spherand-type calixarene [J].
Agbaria, K ;
Biali, SE ;
Böhmer, V ;
Brenn, J ;
Cohen, S ;
Frings, M ;
Grynszpan, F ;
Harrowfield, JM ;
Sobolev, AN ;
Thondorf, I .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :2900-2906
[6]   Spirodienone derivatives of a spherand-type calixarene [J].
Agbaria, K ;
Aleksiuk, O ;
Biali, SE ;
Böhmer, V ;
Frings, M ;
Thondorf, I .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :2891-2899
[7]   SELECTIVE HYDROXYL REPLACEMENT IN CALIXARENES - AMINOCALIXARENE, AZOCALIXARENE, AND XANTHENOCALIXARENE DERIVATIVES [J].
ALEKSIUK, O ;
COHEN, S ;
BIALI, SE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (38) :9645-9652
[8]   NAFION-H CATALYZED FRIEDEL-CRAFTS REACTION OF METHYLENE GROUPS - PREPARATION OF [9,9']SPIROBIXANTHENE [J].
ALEKSIUK, O ;
BIALI, SE .
TETRAHEDRON LETTERS, 1993, 34 (30) :4857-4860
[9]  
Aleksiuk O, 1996, NEW J CHEM, V20, P473
[10]   SPIRODIENONE ROUTE FOR AMINODEHYDROXYLATION - MONOAMINOTRIHYDROXY-P-TERT-BUTYLCALIX[4]ARENE [J].
ALEKSIUK, O ;
GRYNSZPAN, F ;
BIALI, SE .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :1994-1996