The cathodic alkylation of ortho-bis(alkyl- and arylsulfonyl)benzenes by alkyl halides in aprotic solution

被引：7

作者：

Cauliez, P ^{[1
]}

Benaskar, M ^{[1
]}

Simonet, J ^{[1
]}

机构：

[1] UNIV RENNES 1,CNRS,LAB ELECTROCHIM,F-35042 RENNES,FRANCE

来源：

ELECTROCHIMICA ACTA | 1997年 / 42卷 / 13-14期

关键词：

electroreduction; ortho-bis(alkyl- and arylsulfonyl)benzenes; alkylation; tert-butylation; radical scavengers;

D O I：

10.1016/S0013-4686(97)85499-0

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

ortho-Bis(alkyl- and arylsulfonyl)benzenes were reduced in aprotic dimethylformamide in the presence of a large excess of alkyl halides. Concomitant alkylation and monocleavage of a C-S bond were observed. Comparison was done particularly between results obtained with primary and tertiary alkyl halides, especially in the presence of radical scavengers. (C) 1997 Elsevier Science Ltd.

引用

页码：2191 / 2199

页数：9

共 24 条

[1] DETERMINATION OF THE LIFETIMES OF UNSTABLE ION RADICALS BY HOMOGENEOUS REDOX CATALYSIS OF ELECTROCHEMICAL REACTIONS - APPLICATION TO THE REDUCTION OF AROMATIC HALIDES [J].

ANDRIEUX, CP ;

BLOCMAN, C ;

DUMASBOUCHIAT, JM ;

MHALLA, F ;

SAVEANT, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3806-3813

[2]

[Anonymous], 1994, ELECT PARAMAGNETIC R

[3] ORTHO-BIS(ALKYLSULFONYL)BENZENES - THE FATE OF THEIR ELECTROCHEMICALLY FORMED ANION RADICAL - SN2 VS CLEAVAGE REACTION [J].

BELKASMIOUI, A ;

SIMONET, J .

TETRAHEDRON LETTERS, 1991, 32 (22) :2481-2484

[4] CATHODIC COUPLING OF 1, 3, 5-TRI (ARYL AND ALKYLSULFONYL) BENZENES INTO TETRA AND PENTA-SUBSTITUTED BIARYLS [J].

BENASKAR, M ;

SIMONET, J .

TETRAHEDRON LETTERS, 1994, 35 (11) :1727-1730

[5]

BENASKAR M, 1994, THESIS U RENNES 1

[6] ON THE STEREOISOMERIZATION OF RADICALS DURING ALIPHATIC NUCLEOPHILIC SUBSTITUTIONS [J].

DAASBJERG, K ;

LUND, T ;

LUND, H .

TETRAHEDRON LETTERS, 1989, 30 (04) :493-496

[7] CATHODIC CLEAVAGE OF HETEROARYLALKYLSULFONES - A FACILE ROUTE TO LONG-CHAIN ALIPHATIC SULFINATES AND RELEVANT SULFONES [J].

DELAUNAY, J ;

MABON, G ;

ELBADRE, MC ;

ORLIAC, A ;

SIMONET, J .

TETRAHEDRON LETTERS, 1992, 33 (16) :2149-2150

[8] POTENTIAL DEPENDENCE OF COUPLING VS REDUCTION IN THE REACTION BETWEEN BENZYL HALIDES AND ANION RADICALS [J].

FUHLENDORFF, R ;

OCCHIALINI, D ;

PEDERSEN, SU ;

LUND, H .

ACTA CHEMICA SCANDINAVICA, 1989, 43 (08) :803-806

[9] UNIMOLECULAR DECOMPOSITION OF T-C4H9 RADICAL [J].

KNYAZEV, VD ;

DUBINSKY, IA ;

SLAGLE, IR ;

GUTMAN, D .

JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (20) :5279-5289

[10] ELECTROGENERATED ANIONS AS ELECTRON-TRANSFER REAGENTS [J].

LUND, H ;

KRISTENSEN, LH .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (07) :495-498

← 1 2 3 →