Dimethyl carbonate as a methylating agent. The selective mono-C-methylation of alkyl aryl sulfones

被引：27

作者：

Bomben, A ^{[1
]}

Selva, M ^{[1
]}

Tundo, P ^{[1
]}

机构：

[1] Univ Venice, Dipartimento Sci Ambientali, I-30123 Venice, Italy

来源：

JOURNAL OF CHEMICAL RESEARCH-S | 1997年 / 12期

关键词：

D O I：

10.1039/a703510a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

At 180-210 degrees C, alpha-methylene sulfones (both benzyl aryl and alkyl aryl sulfones, RCH(2)SO(2)AR: R = Ph, p-ClC6H4, Ar = Ph p-ClC6H4, p-MeC6H4, and R = Me, Ar = Ph, p-ClC6H4, p-MeC6H4) react with dimethyl carbonate to yield the corresponding mono-C-methyl derivatives [RCH(CH3)SO2Ar] in a selectivity > 99%, at conversions of 76-99% (isolated yields: 97-92%).

引用

页码：448 / 449

页数：3

共 23 条

[1] A NEW SYNTHESIS OF 2-ARYLOXYPROPIONIC ACIDS DERIVATIVES VIA SELECTIVE MONO-C-METHYLATION OF METHYL ARYLOXYACETATES AND ARYLOXYACETONITRILES WITH DIMETHYL CARBONATE [J].

BOMBEN, A ;

MARQUES, CA ;

SELVA, M ;

TUNDO, P .

TETRAHEDRON, 1995, 51 (42) :11573-11580

[2] NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTIONS OF UNACTIVATED ARYL HALIDES WITH THIOLATE IONS IN HEXAMETHYLPHOSPHORAMIDE [J].

COGOLLI, P ;

MAIOLO, F ;

TESTAFERRI, L ;

TINGOLI, M ;

TIECCO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2642-2646

[3] OXIDATIVE CARBONYLATION OF METHANOL TO DIMETHYL CARBONATE (DMC) - A NEW CATALYTIC-SYSTEM [J].

DELLEDENNE, D ;

RIVETTI, F ;

ROMANO, U .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 488 (1-2) :C15-C19

[4]

GOLINSKI J, 1979, SYNTHESIS-STUTTGART, P461

[5] DICARBANIONS OF DIBENZYL KETONE, DIBENZYL SULFONE AND ALPHA,BETA,BETA-TRIPHENYLPROPIONITRILE [J].

HAUSER, CR ;

HARRIS, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (23) :6342-6342

[6] TRIFLONES (CF3SO2C) - SURVEY OF REACTIVITY AND SYNTHETIC UTILITY [J].

HENDRICKSON, JB ;

GIGA, A ;

WAREING, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (07) :2275-2276

[7]

KAISER EM, 1967, TETRAHEDRON LETT, P3341

[8]

KOLBINA NM, 1976, ZH ORG KHIM+, V12, P1708

[9]

KONDO K, 1975, TETRAHEDRON LETT, P1007

[10] THE POLARITY OF THE OXY SULFUR BOND IN DIMETHYLSULFOXIDE AND SULFONE, ALKYLPHENYL AND ALKYL-2-PYRAZINYL SULFONES [J].

LUMBROSO, H ;

CURE, J ;

KONAKAHARA, T ;

SATO, K .

JOURNAL OF MOLECULAR STRUCTURE, 1983, 98 (3-4) :277-295

← 1 2 3 →