Benzylation of alcohols and phenols with N-(4-methoxybenzyl)-o-benzenedisulfonimide

被引：10

作者：

Carlsen, PHJ ^{[1
]}

机构：

[1] Norwegian Univ Sci & Technol, Dept Organ Chem, N-7034 Trondheim, Norway

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(98)00091-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(4-methoxybenzyl)-o-benzene disulfonimide was prepared from o-benzenedisulfonyl chloride and 4-methoxybenzylamin in dichloromethane. Reaction of this compound with alcohols or phenols undere basic conditions gave the corresponding 4-methoxybenzyl ethers in good yields. Primary alkylamines were converted to the corresponding alcohols by treating the benzenedisulfonimido derivative with aqueous KOH in DMF solution. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1799 / 1802

页数：4

共 13 条

[1] A NEW METHOD FOR THE PROTECTION OF THE SULFHYDRYL GROUP DURING PEPTIDE SYNTHESIS [J].

AKABORI, S ;

SAKAKIBARA, S ;

SHIMONISHI, Y ;

NOBUHARA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1964, 37 (03) :433-434

[2] THE PARA-METHOXYBENZYL GROUP AS PROTECTIVE GROUP OF THE ANOMERIC CENTER - SELECTIVE CONVERSIONS OF HYDROXY-GROUPS INTO BROMO GROUPS IN PARA-METHOXYBENZYL 2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE [J].

CLASSON, B ;

GAREGG, PJ ;

SAMUELSSON, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05) :419-422

[3] SELECTIVE, ELECTROPHILIC FLUORINATIONS USING N-FLUORO-O-BENZENEDISULFONIMIDE [J].

DAVIS, FA ;

HAN, W ;

MURPHY, CK .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4730-4737

[4]

FUKUYAMA T, 1985, TETRAHEDRON LETT, V26, P6391

[5] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS [J].

HORITA, K ;

YOSHIOKA, T ;

TANAKA, T ;

OIKAWA, Y ;

YONEMITSU, O .

TETRAHEDRON, 1986, 42 (11) :3021-3028

[6] INVERSION OF CHIRAL ALPHA-METHYLBENZYLAMINE [J].

JOHANSEN, C ;

FIKSDAHL, A .

CHIRALITY, 1994, 6 (02) :161-164

[7] UNTERSUCHUNGEN UBER AROMATISCHE DIAZOVERBINDUNGEN .2. VERFAHREN ZUR HERSTELLUNG AROMATISCHER SULFONSAURECHLORIDE, EINE NEUE MODIFIKATION DER SANDMEYERSCHEN REAKTION [J].

MEERWEIN, H ;

DITTMAR, G ;

GOLLNER, R ;

HAFNER, K ;

MENSCH, F ;

STEINFORT, O .

CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (06) :841-852

[8] NUCLEOPHILIC-SUBSTITUTION OF CHIRAL AMINE N,N-DITOSYLDERIVATIVES [J].

OPPEDAL, H ;

TVEIT, IC ;

FIKSDAHL, A .

TETRAHEDRON-ASYMMETRY, 1994, 5 (05) :895-902

[9] 2 NEW PROCEDURES FOR THE INTRODUCTION OF BENZYL-TYPE PROTECTING GROUPS FOR THIOLS [J].

RICHTER, LS ;

MARSTERS, JC ;

GADEK, TR .

TETRAHEDRON LETTERS, 1994, 35 (11) :1631-1634

[10] THE SYNTHESIS OF (S)-1-METHYL-3-PHENYLPROPYLAMINE BY INVERSION OF AMINES [J].

SELJESTOKKEN, B ;

FIKSDAHL, A .

ACTA CHEMICA SCANDINAVICA, 1993, 47 (10) :1050-1052

← 1 2 →