Scandium triflate-catalyzed cyclocondensation of 1,3-dialkoxybenzenes with 1,3,5-trioxane. Formation of resorcin[4]arenes and confused resorcin[4]arenes

被引：8

作者：

Morikawa, Osamu ^{[1
]}

Nagamatsu, Yoshihisa ^{[1
]}

Nishimura, Akihiko ^{[1
]}

Kobayashi, Kazuhiro ^{[1
]}

Konishi, Hisatoshi ^{[1
]}

机构：

[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 24期

关键词：

resorcinarene; metacyclophane; crystal structure;

D O I：

10.1016/j.tetlet.2006.04.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclocondensation of 1,3-dialkoxybenzenes with 1,3,5-trioxane was catalyzed by Sc(OTf)(3) to produce resorcin[4]arene octaalkyl ethers as the major products. In addition, 'confused' resorcin[4]arene octaalkyl ethers bearing one alkoxy group at the intra-annular position were obtained as the minor products. The variable temperature H-1 NMR spectroscopy showed that the alkoxy group at the intra-annular position cannot pass through the macrocyclic annulus, indicating a rigid molecular framework. The structure of the ethoxy derivative of the confused resorcin[4]arene was determined by X-ray crystallography. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3991 / 3994

页数：4

共 35 条

[1] Sc(OTf)3-catalyzed cyclocondensation of 2-propylresorcinol with diethoxymethane.: Formation and fragmentation of resorcin[n]arenes
Morikawa, O
Yanagimoto, M
Sakakibara, H
Kobayashi, K
Konishi, H
[J]. TETRAHEDRON LETTERS, 2004, 45 (29) : 5731 - 5734
[2] Solvent provides a trap for the guest-induced formation of 1D host frameworks based upon supramolecular, deep-cavity resorcin[4]arenes
MacGillivray, Leonard R.
Reid, Jennifer L.
Ripmeester, John A.
[J]. CRYSTENGCOMM, 1999, (01):
[3] 1,3,5-Cycloheptatrienyl derivatives of calix[4]- and calix[6]arenes and their corresponding tropylium salts
Wendel, V
Abraham, W
[J]. TETRAHEDRON LETTERS, 1997, 38 (07) : 1177 - 1180
[4] Rhodium(III)-Catalyzed Asymmetric [4+1] and [5+1] Annulation of Arenes and 1,3-Enynes: A Distinct Mechanism of Allyl Formation and Allyl Functionalization
Sun, Jiaqiong
Yuan, Weiliang
Tian, Rong
Wang, Peiyuan
Zhang, Xue-Peng
Li, Xingwei
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (50) : 22706 - 22713
[5] Host-guest inclusion systems of tetra(alkyl)resorcin [4]arenes with choline in DMSO: Dynamic NMR studies and X-ray structural characterization of the 1:1 inclusion complex
Velasquez-Silva, Astrid
Sarmiento Forero, Roger
Sanabria, Edilma
Perez-Redondo, Adrian
Maldonado, Mauricio
[J]. JOURNAL OF MOLECULAR STRUCTURE, 2019, 1198
[6] Stereocontrol in rare earth metal triflate-catalyzed 1,3-dipolar cycloaddition reaction of 2-benzopyrylium-4-olate with aldehydes
Suga, H
Kakehi, A
Ito, S
Inoue, K
Ishida, H
Ibata, T
[J]. ORGANIC LETTERS, 2000, 2 (20) : 3145 - 3148
[7] Theoretical study of the conformational isomerism of 2,4,6-substituted 1,3,5-trimethoxycalix[6]arenes
van Hoorn, WP
van Veggel, FCJM
Reinhoudt, DN
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (33): : 6676 - 6681
[8] Asymmetric synthesis of 2-alkyl-4-hydroxycyclohex-2-en-1-ones by scandium(III) triflate-catalyzed fragmentation of 2-alkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones
Matsuo, Jun-ichi
Kawano, Mizuki
Takeuchi, Kosuke
Tanaka, Hiroyuki
Ishibashi, Hiroyuki
[J]. TETRAHEDRON LETTERS, 2009, 50 (17) : 1917 - 1919
[9] Access to Pyridyl-Substituted 1,3,5-Triazines from 4H-Pyrido[1,3]oxazin-4-ones via a Cyclocondensation Process
Le Falher, Laetitia
Ben Ayad, Omar
Ziyaret, Ozge
Mamontov, Alexander
Botuha, Candice
Thorimbert, Serge
Slowinski, Franck
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14): : 6579 - 6589
[10] Recyclable gallium(III) triflate-catalyzed [4+3] cycloaddition for synthesis of 2,4-disubstituted-3H-benzo[b][1,4]diazepines
Huang, Shi-Gang
Mao, Hai-Feng
Zhou, Shao-Fang
Zou, Jian-Ping
Zhang, Wei
[J]. TETRAHEDRON LETTERS, 2013, 54 (46) : 6178 - 6180

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