p-(benzyloxy)calix[8]arene: One-pot synthesis and functionalization

被引：27
|
作者：
Casnati, A [1 ]
Ferdani, R [1 ]
Pochini, A [1 ]
Ungaro, R [1 ]
机构：
[1] UNIV PARMA,DIPARTIMENTO CHIM ORGAN & IND,I-43100 PARMA,ITALY
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 18期
关键词：
D O I：
10.1021/jo970620r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The condensation of hydroquinone monobenzyl ether in the presence of several bases gives a mixture of cyclic oligomers. Using p-benzyloxyphenol, paraformaldehyde, and NaOH in 45:82:1 molar ratio in refluxing xylene, p-(benzyloxy)calix[8]arene (2) was selectively produced in 48% isolated yield. Compound 2 was also functionalized at the lower rim with acetoxy, methyl, pentyl, [(ethyloxy)carbonyl]methyl, and [(N,N-diethylamino)carbonyl]methyl groups. Replacement of the benzyl groups on these compounds allowed for the first time the high-yield syntheses of calix[8]hydroquinone and its derivatives.
引用
收藏
页码：6236 / 6239
页数：4
相关论文
共 50 条
  • [1] p-(Benzyloxy)calix[8]arene: One-Pot Synthesis and Functionalization
    Casnati, A.
    Ferdani, R.
    Pochini, A.
    Ungaro, R.
    Journal of Organic Chemistry, 62 (18):
  • [2] p-(Benzyloxy)calix[8]arene Synthesis Revisited: p-(Benzyloxy)calix[4]-, p-(Benzyloxy)calix[5]-, p-(Benzyloxy)calix[7]-, and p-(Benzyloxy)bis(homooxa)calix[4]arenes
    Huc, Vincent
    Npetgat, Eloine
    Guerineau, Vincent
    Bourcier, Sophie
    Dos Santos, Amandine
    Guillot, Regis
    Baltaze, Jean-Pierre
    Martini, Cyril
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (32) : 6186 - 6192
  • [3] A one-pot synthesis and functionalization of polyynes
    Morisaki, Y
    Luu, T
    Tykwinski, RR
    ORGANIC LETTERS, 2006, 8 (04) : 689 - 692
  • [4] One-pot synthesis of oxygen and nitrogen-bridged calix[2]arene[2]triazines
    Wang, Xu-Dong
    Wang, De-Xian
    Huang, Zhi-Tang
    Wang, Mei-Xiang
    SUPRAMOLECULAR CHEMISTRY, 2014, 26 (7-8) : 601 - 606
  • [5] SYNTHESIS OF P-(1-ADAMANTYL)CALIX[4]ARENE AND P-(3-SUBSTITUTED-1-ADAMANTYL)CALIX[4]ARENE
    KHOMICH, AN
    SHOKOVA, EA
    KOVALEV, VV
    SYNLETT, 1994, (12) : 1027 - 1028
  • [6] One-pot synthesis and functionalization of resorcinarene nanocapsules
    Balasubramanian, Ramjee
    Kalaitzis, Zaharoula M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [7] A one-step, one-pot synthesis of p-acyl calix[n]arenes
    Kumar, S
    Chawla, HM
    Varadarajan, R
    TETRAHEDRON LETTERS, 2002, 43 (14) : 2495 - 2498
  • [8] An expedient one-pot synthesis of para-tert-butylcalix[8]- and [9]arene
    Bew, Sean P.
    Sharma, Sunil V.
    CHEMICAL COMMUNICATIONS, 2007, (09) : 975 - 977
  • [9] Conjugated p-(tetrathiafulvalenylmethylideneamino)calix[4]arene
    Regnouf-De-Vains, JB
    Salle, M
    Lamartine, R
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (12): : 2461 - 2462
  • [10] C3v (Trimethyl) p-(Benzyloxy)calix[6]arene: A Versatile Platform for the Synthesis of Functionalized C3v Calix[6]arenes
    Huc, Vincent
    Guerineau, Vincent
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (11) : 2199 - 2205
12345