SYNTHESIS OF AZOPHENOLIC CROWN-ETHERS OF C-S SYMMETRY INCORPORATING CIS-1-PHENYLCYCLOHEXANE-1,2-DIOL RESIDUES AS A STERIC BARRIER AND DIASTEREOTOPIC FACE SELECTIVITY IN COMPLEXATION OF AMINES BY THEIR DIASTEREOTOPIC FACES

被引：13

作者：

NAEMURA, K ^{[1
]}

TAKEUCHI, S ^{[1
]}

ASADA, M ^{[1
]}

UENO, K ^{[1
]}

HIROSE, K ^{[1
]}

TOBE, Y ^{[1
]}

KANEDA, T ^{[1
]}

SAKATA, Y ^{[1
]}

机构：

[1] OSAKA UNIV,INST SCI & IND RES,IBARAKI,OSAKA 567,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 11期

关键词：

D O I：

10.1039/p19950001429

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Azophenolic crown ethers 1 and 2 of C-s symmetry incorporating cis-1-phenylcyclohexane-1,2-diol residues as a steric barrier have been prepared. Diastereotopic face selectivity in complexation with 2-methoxyethylamine, n-propylamine and ethanolamine was examined using temperature-dependent H-1 NMR spectroscopy. Both bind ethanolamine stereoselectively to one of their diaseereotopic faces; the prediction of which diastereoisomeric complexwas preferentially formed is made on the basis of a CPK molecular-model examination ofthe complexes.

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页码：1429 / 1435

页数：7

相关论文

共 10 条

[1] A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].

BENESI, HA ;

HILDEBRAND, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707

[2] THERMODYNAMIC AND KINETIC DATA FOR MACROCYCLE INTERACTION WITH CATIONS AND ANIONS [J].

IZATT, RM ;

PAWLAK, K ;

BRADSHAW, JS ;

BRUENING, RL .

CHEMICAL REVIEWS, 1991, 91 (08) :1721-2085

[3] CHIRAL AZOPHENOLIC ACERANDS - COLOR INDICATORS TO JUDGE THE ABSOLUTE-CONFIGURATION OF CHIRAL AMINES [J].

KANEDA, T ;

HIROSE, K ;

MISUMI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :742-743

[4] SYNTHESIS, COLORATION, AND CRYSTAL-STRUCTURE OF THE DIBASIC CHROMOACERAND PIPERAZINE 1-1 SALT COMPLEX [J].

KANEDA, T ;

ISHIZAKI, Y ;

MISUMI, S ;

KAI, Y ;

HIRAO, G ;

KASAI, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2970-2972

[5] STEREOSELECTIVITY IN COMPLEXATION OF PRIMARY ALKYLAMMONIUM CATIONS BY DIASTEREOTOPIC FACES OF CHIRAL ASYMMETRIC CROWNS [J].

LAIDLER, DA ;

STODDART, JF .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (14) :481-483

[6] NUCLEAR METHYLATION OF SOME PHENOLIC COMPOUNDS [J].

MORAN, WJ ;

SCHREIBER, EC ;

ENGEL, E ;

BEHN, DC ;

YAMINS, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (01) :127-129

[7] THE SYNTHESIS OF AZOPHENOLIC CROWN-ETHERS OF C(S) SYMMETRY INCORPORATING CIS-1-PHENYLCYCLOHEXANE-1,2-DIOL RESIDUES AND DIASTEREOTOPIC FACE SELECTIVITY IN COMPLEXATION OF ETHANOLAMINE BY THEIR DIASTEREOTOPIC FACES [J].

NAEMURA, K ;

TAKEUCHI, S ;

ASADA, M ;

HIROSE, K ;

TOBE, Y ;

KANEDA, T ;

SAKATA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :711-712

[8] PREPARATION AND ENANTIOMER RECOGNITION BEHAVIOR OF CROWN-ETHERS CONTAINING CIS-1-PHENYLCYCLOHEXANE-1,2-DIOL AND TRANS-1,2-DIPHENYLCYCLOHEXANE-1,2-DIOL AS A CHIRAL SUBUNIT [J].

NAEMURA, K ;

MIYABE, H ;

SHINGAI, Y ;

TOBE, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09) :1073-1077

[9] AZOPHENOLIC ACERANDS HAVING CHIRAL 1-PHENYL-CIS-1,2-CYCLOHEXANEDIOL UNITS - A CORRELATION BETWEEN ENANTIORECOGNITIVE COLORATION AND HOST-GUEST COMPLEMENTARITY [J].

NAEMURA, K ;

UENO, K ;

TAKEUCHI, S ;

TOBE, Y ;

KANEDA, T ;

SAKATA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8475-8476

[10]

PETTMAN RB, 1979, TETRAHEDRON LETT, P457