Synthesis of p-tert-butylthiacalix[n]arenes (n=4, 6, and 8) from a sulfur-bridged acyclic dimer of p-tert-butylphenol

被引：42

作者：

Kon, N ^{[1
]}

Iki, N ^{[1
]}

Miyano, S ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Engn, Dept Biomol Engn, Aoba Ku, Sendai, Miyagi 9808579, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 12期

关键词：

calixarenes; thiacalixarenes; sulfide;

D O I：

10.1016/S0040-4039(02)00214-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-step method for the synthesis of p-tert-butylthiacalix[n]arenes TCnAs (n=4 and 6) by reacting p-tert-butylphenol I with elemental sulfur in the presence of a base was advantageously replaced by a two-step procedure in which a sulfur-bridged linear dimer of I was prepared first to use as the starting material for the cyclo-condensation with sulfur to greatly improve the yields of TC4A (83%.) and TC6A (5.3%). The present dimer method allowed the isolation of TC8A in an appreciable amount (4.3%) for the first time. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2231 / 2234

页数：4

共 24 条

[1] Systematic structural coordination chemistry of p-tert-butyltetrathiacalix[4]arene:: 1.: Group 1 elements and congeners [J].

Bilyk, A ;

Hall, AK ;

Harrowfield, JM ;

Hosseini, MW ;

Skelton, BW ;

White, AH .

INORGANIC CHEMISTRY, 2001, 40 (04) :672-686

[2] CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].

BOHMER, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745

[3]

Bohmer V, 1997, LIEBIGS ANN-RECL, P2019

[4]

Gutsche C.D., 1989, MONOGRAPHS SUPRAMOLE

[5]

Gutsche C. D, 1998, MONOGRAPHS SUPRAMOLE

[6] Synthesis of p-tert-butylthiacalix[4]arene and its inclusion property [J].

Iki, N ;

Kabuto, C ;

Fukushima, T ;

Kumagai, H ;

Takeya, H ;

Miyanari, S ;

Miyashi, T ;

Miyano, S .

TETRAHEDRON, 2000, 56 (11) :1437-1443

[7] Crystal structure and inclusion property of p-tert-butylthiacalix [6]arene [J].

Iki, N ;

Morohashi, N ;

Suzuki, T ;

Ogawa, S ;

Aono, M ;

Kabuto, C ;

Kumagai, H ;

Takeya, H ;

Miyanari, S ;

Miyano, S .

TETRAHEDRON LETTERS, 2000, 41 (15) :2587-2590

[8]

IKI N, 2001, J CHEM SOC JPN CHEM, P609

[9]

IKI N, IN PRESS J INCL PHEN

[10] Calix[4]arenes comprised of aniline units [J].

Katagiri, H ;

Iki, N ;

Hattori, T ;

Kabuto, C ;

Miyano, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :779-780

← 1 2 3 →