THE MECHANISM OF DEAMINATION OF METHOXY SUBSTITUTED TRITYLAMMONIUM IONS IN METHANOLIC AQUEOUS ACID

被引：24

作者：

BLEASDALE, C ^{[1
]}

GOLDING, BT ^{[1
]}

LEE, WH ^{[1
]}

MASKILL, H ^{[1
]}

RISEBOROUGH, J ^{[1
]}

SMITS, E ^{[1
]}

机构：

[1] UNIV NEWCASTLE UPON TYNE,DEPT CHEM,NEWCASTLE TYNE NE1 7RU,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 01期

关键词：

D O I：

10.1039/c39940000093

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In methanolic aqueous acid, methoxy-substituted tritylammonium ions undergo heterolysis to give an equilibrium mixture of the substituted trityl cation, the corresponding alcohol (and methyl ether), and the ammonium cation via an S(N)1 mechanism; the detection of a reaction channel first order in hydronium ions may implicate substituted trityl cation-ammonia (ion-molecule) pairs as reactive intermediates.

引用

页码：93 / 94

页数：2

共 14 条

[1] NEW APPLICATIONS OF THE PROTECTING GROUP DI-(4-METHOXYPHENYL)METHYL - N-PROTECTION OF URETHANES AND URIDINES, AND EFFICIENT REMOVAL BY EITHER CERIC AMMONIUM-NITRATE SILICA OR 2,3-DICHLORO-5,6-DICYANOQUINONE [J].

ABUSBEIH, K ;

BLEASDALE, C ;

GOLDING, BT ;

KITSON, SL .

TETRAHEDRON LETTERS, 1992, 33 (33) :4807-4810

[2] HYDROLYZES OF TERPENOID DIPHOSPHATES - EFFECTS OF AZIDE ION ON PRODUCTS OF HYDROLYSIS [J].

ALARCON, M ;

CORI, O ;

ROJAS, MC ;

PAVEZ, H ;

BACALOGLU, R ;

BUNTON, CA .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1992, 5 (02) :83-92

[3]

Albert A., 1962, IONIZATION CONSTANTS

[4] CONCURRENT STEPWISE AND CONCERTED SUBSTITUTION-REACTIONS OF 4-METHOXYBENZYL DERIVATIVES AND THE LIFETIME OF THE 4-METHOXYBENZYL CARBOCATION [J].

AMYES, TL ;

RICHARD, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9507-9512

[5] SECONDARY DEUTERIUM KINETIC ISOTOPE EFFECTS IN THE SOLVOLYSIS OF 4-TERT-BUTYLCYCLOHEXYL AND BICYCLO[3.2.1]OCTAN-3-YL TOLUENE-PARA-SULFONATES - NEW RESULTS USING 50-PERCENT-AQUEOUS ETHANOL, ACETIC-ACID, AND 97-PERCENT-AQUEOUS HEXAFLUOROPROPAN-2-OL [J].

BANKS, RM ;

MASKILL, H ;

NATARAJAN, R ;

WILSON, AA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (02) :427-431

[6]

Fersht A, 1977, ENZYME STRUCTURE MEC

[7] RATE AND PRODUCT ANALYTICAL STUDY OF THE SOLVOLYSIS OF 3-CHLOROBENZYL ARENESULFONATES IN AQUEOUS 2,2,2-TRIFLUOROETHANOL [J].

GORDON, IM ;

MASKILL, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (12) :1951-1953

[8] BOND DISSOCIATION ENERGIES BY KINETIC METHODS [J].

KERR, JA .

CHEMICAL REVIEWS, 1966, 66 (05) :465-&

[9] REACTIVITIES OF DIARYLMETHYL AND TRIARYLMETHYL CATIONS WITH PRIMARY AMINES IN AQUEOUS ACETONITRILE SOLUTIONS - THE IMPORTANCE OF AMINE HYDRATION [J].

MCCLELLAND, RA ;

KANAGASABAPATHY, VM ;

BANAIT, NS ;

STEENKEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1816-1823

[10]

TAFT RW, 1975, PROTON TRANSFER REAC, pCH5

← 1 2 →