Diester intrabridging of p-tert-butylcalix[8]arene and unexpected formation of the monospirodienone derivative

被引：10
作者：
Consoli, GML
Geraci, C
Cunsolo, F
Neri, P
机构：
[1] CNR, Ist Chim Biomol, Sez Catania, I-95028 Valverde, CT, Italy
[2] Univ Salerno, Dipartimento Chim, I-84081 Baronissi, SA, Italy
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 01期
关键词：
calixarenes; calix[8]arenes; intrabridged esters; oxidation; monospirodienone;
D O I：
10.1016/S0040-4039(02)02485-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of p-tert-butylcalix[8]arene 1 with adipoyl chloride in the presence of NaH as the base yielded singly and doubly intrabridged esters 2-4 and 6. Surprisingly, calix[8]arene monospirodienone derivative 7 was also isolated, which was originated by 0, oxidation. The conditions of this oxidation were optimized leading to a novel synthetic approach to calixarene monospirodienones based on the O-2/NaH/acyl-chloride oxidizing system. Xantheno calix[8]arenes 8-8a were obtained by rearrangement of 7. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：53 / 56
页数：4
相关论文
共 50 条
[31]   Contribution to protonated tetraethyl p-tert-butylcalix[4]arene tetraacetate: stability and DFT calculated structure [J].
Emanuel Makrlík ;
Jiří Dybal ;
Petr Vaňura .
Monatshefte für Chemie - Chemical Monthly, 2009, 140 :29-32
[32]   Synthesis of two new p-tert-butylcalix[4]arene β-ketoimin derivatives for extraction of dichromate anion [J].
Bayrakci, Mevlut ;
Ertul, Seref ;
Sahin, Ozlem ;
Yilmaz, Mustafa .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2009, 63 (3-4) :241-247
[33]   New diamino derivatives of p-tert-butylcalix[4]arene for oxyanion recognition: synthesis and complexation studies [J].
Yilmaz, Aydan ;
Tabakci, Begum ;
Tabakci, Mustafa .
SUPRAMOLECULAR CHEMISTRY, 2009, 21 (06) :435-441
[34]   Contribution to protonated tetraethyl p-tert-butylcalix[4]arene tetraacetate: stability and DFT calculated structure [J].
Makrlik, Emanuel ;
Dybal, Jiri ;
Vanura, Petr .
MONATSHEFTE FUR CHEMIE, 2009, 140 (01) :29-32
[35]   The hydrogen bonding and conformations of p-tert-butylcalix[4]arene as studied by IR spectroscopy and by DFT calculations [J].
Furer, VL ;
Borisoglebskaya, EI ;
Zverev, VV ;
Kovalenko, VI .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2005, 62 (1-3) :483-493
[36]   Absorption of Chlorinated Hydrocarbons Dissolved in Water with Pellets Made of p-tert-Butylcalix[4]arene and Silica Gel [J].
Morohashi, Naoya ;
Shibata, Ozora ;
Hattori, Tetsutaro .
CHEMISTRY LETTERS, 2012, 41 (11) :1412-1413
[37]   Cation complexation with p-tert-butylcalix[5]arene pentacarboxylic acid derivative: An allosteric regulation of the first metal ion for stepwise extraction of the second ion [J].
Adhikari, Birendra Babu ;
Gurung, Manju ;
Kawakita, Hidetaka ;
Ohto, Keisuke .
ANALYST, 2011, 136 (18) :3758-3769
[38]   A Novel De-tert-butylation of p-tert-Butylcalix[n]arenes [J].
Chennakesavulu, K. ;
Raju, G. Bhaskar ;
Prabhakar, S. .
ASIAN JOURNAL OF CHEMISTRY, 2010, 22 (07) :5513-5516
[39]   Protonation of electroneutral p-tert-butylcalix[4]arenetetraacetic acid [J].
Jaroslav Kříž ;
Jiří Dybal ;
Emanuel Makrlík ;
Jan Budka ;
Petr Vaňura .
Monatshefte für Chemie - Chemical Monthly, 2010, 141 :19-22
[40]   Microwave-assisted alkylation of p-tert-butylcalix[4]arene lower rim: the effect of alkyl halides [J].
Burilov, Vladimir A. ;
Nugmanov, Ramil I. ;
Ibragimova, Regina R. ;
Solovieva, Svetlana E. ;
Antipin, Igor S. ;
Konovalov, Alexander I. .
MENDELEEV COMMUNICATIONS, 2013, 23 (02) :113-115
12345