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
[21]   Competitive Inclusion of Disubstituted Benzene Regioisomers with Crystals of p-tert-Butylcalix[4]arene [J].
Morohashi, Naoya ;
Tonosaki, Ayano ;
Kitagawa, Taro ;
Sasaki, Takuro ;
Ebata, Kohei ;
Hattori, Tetsutaro .
CRYSTAL GROWTH & DESIGN, 2017, 17 (10) :5038-5043
[22]   Amphiphilic p-tert-butylcalix[4]arene scaffolds containing exposed carbohydrate dendrons [J].
Roy, R ;
Kim, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (03) :369-372
[23]   Simulations of p-tert-butylcalix[4]arene with multiple occupancies of small guest molecules [J].
Alavi, Saman ;
Ripmeester, John A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (06) :1965-1971
[24]   Hydrogen Adsorption and Diffusion in p-tert-Butylcalix[4]arene: An Experimental and Molecular Simulation Study [J].
Alavi, Saman ;
Woo, Tom K. ;
Sirjoosingh, Andrew ;
Lang, Stephen ;
Moudrakovski, Igor ;
Ripmeester, John A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (38) :11689-11696
[25]   DFT-calculated structure of protonated tetraphenyl p-tert-butylcalix[4]arene tetraketone [J].
Dybal, Jiri ;
Makrlik, Emanuel ;
Budka, Jan ;
Vanura, Petr .
MONATSHEFTE FUR CHEMIE, 2008, 139 (11) :1353-1355
[26]   Synthesis of N-phtaloyl amino acid p-tert-butylcalix[4]arene esters [J].
Lazzarotto, M ;
Nachtigall, FF ;
Nome, F .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (02) :255-258
[27]   Protonated tetramethyl p-tert-butylcalix[4]arene tetraketone:: NMR evidence and probable structures [J].
Kriz, Jaroslav ;
Dybal, Jiri ;
Makrlik, Emanuel ;
Budka, Jan ;
Vanura, Petr .
MONATSHEFTE FUR CHEMIE, 2007, 138 (08) :735-740
[28]   Simultaneous Determination of Thallium and Lead on a Chemically Modified Electrode with Langmuir-Blodgett Film of a p-tert-Butylcalix[4]arene Derivative [J].
Zou, Lina ;
Zhang, Yufeng ;
Qin, Haili ;
Ye, Baoxian .
ELECTROANALYSIS, 2009, 21 (23) :2563-2568
[29]   A Mn5II tetragonal pyramid stabilized by p-tert-butylcalix[8]arene: Synthesis, structure and magnetic property [J].
Du, Shangchao ;
Ke, Hongshan ;
Bi, Yanfeng ;
Tan, Huaqiao ;
Yu, Yang ;
Tang, Jinkui ;
Liao, Wuping .
INORGANIC CHEMISTRY COMMUNICATIONS, 2013, 29 :85-88
[30]   Synthesis and crystal structures of mono-potassium salts of calix[4]arene and p-tert-butylcalix[4]arene [J].
Hanna, TA ;
Liu, LH ;
Zakharov, LN ;
Rheingold, AL ;
Watson, WH ;
Gutsche, CD .
TETRAHEDRON, 2002, 58 (48) :9751-9757
12345