ON THE ORIGIN OF THE DISTAL VS PROXIMAL REGIOSELECTIVITY IN DI-O-ALKYLATION OF CALIX[4]ARENES

被引：27

作者：

ARAKI, K ^{[1
]}

IWAMOTO, K ^{[1
]}

SHIGEMATSU, S ^{[1
]}

SHINKAI, S ^{[1
]}

机构：

[1] KYUSHU UNIV, FAC ENGN, DEPT ORGAN SYNTH, FUKUOKA 812, JAPAN

来源：

CHEMISTRY LETTERS | 1992年 / 06期

关键词：

D O I：

10.1246/cl.1992.1095

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The mechanistic basis of the distal vs. proximal regioselectivity in di-O-alkylation of calix[4]arene was investigated through the detailed product analyses. It was found that (i) the regioselectivity is profoundly affected by the residual intramolecular hydrogen-bonds and (ii) the distal isomer is more reactive for further O-alkylation than the proximal isomer, resulting in the "apparent" proximal selectivity.

引用

页码：1095 / 1098

页数：4

共 8 条

[1] ON THE CONFORMATIONAL ISOMERS IN TETRA-O-ALKYLCALIX[4]ARENES
ARAKI, K
IWAMOTO, K
SHINKAI, S
MATSUDA, T
[J]. CHEMISTRY LETTERS, 1989, (10) : 1747 - 1750
[2] CALIX[4]ARENES WITH PYRIDINE PENDANT GROUPS - REGIOSELECTIVE PROXIMAL ALKYLATION AT THE LOWER RIM
BOTTINO, F
GIUNTA, L
PAPPALARDO, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) : 5407 - 5409
[3] SYN-1,2-DIALKYLATED CALIX[4]ARENES - GENERAL INTERMEDIATES IN THE NAH/DMF TETRAALKYLATION OF CALIX[4]ARENES
GROENEN, LC
RUEL, BHM
CASNATI, A
TIMMERMAN, P
VERBOOM, W
HARKEMA, S
POCHINI, A
UNGARO, R
REINHOUDT, DN
[J]. TETRAHEDRON LETTERS, 1991, 32 (23) : 2675 - 2678
[4] CALIXARENES .25. CONFORMATIONS AND STRUCTURES OF THE PRODUCTS OF ARYLMETHYLATION OF CALIX[4]ARENES
GUTSCHE, CD
REDDY, PA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) : 4783 - 4791
[5] CORRECTION
IWAMOTO, K
[J]. TETRAHEDRON LETTERS, 1991, 32 (07) : 830 - 830
[6] CONFORMATIONS AND STRUCTURES OF TETRA-O-ALKYL-PARA-TERT-BUTYLCALIX[4]ARENES - HOW IS THE CONFORMATION OF CALIX[4]ARENES IMMOBILIZED
IWAMOTO, K
ARAKI, K
SHINKAI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) : 4955 - 4962
[7] REMARKABLE METAL TEMPLATE EFFECTS ON SELECTIVE SYNTHESES OF PARA-TERT-BUTYLCALIX[4]ARENE CONFORMERS
IWAMOTO, K
FUJIMOTO, K
MATSUDA, T
SHINKAI, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (49) : 7169 - 7172
[8] PKA DETERMINATION OF WATER-SOLUBLE CALIX[4]ARENES
SHINKAI, S
ARAKI, K
GROOTENHUIS, PDJ
REINHOUDT, DN
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (12): : 1883 - 1886

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