Electronic effects of icosahedral carboranes, Friedel-Crafts acylation of 1-phenyl-1,2-, 1,7-, and 1, 12-dicarba-closo-dodecaboranes

被引：14

作者：

Endo, Y ^{[1
]}

Taoda, Y ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 51期

关键词：

carboranes; electronic effects; Friedel-Crafts reactions;

D O I：

10.1016/S0040-4039(99)01911-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Friedel-Crafts acylation of the benzene nucleus of 1-phenyl-1,2-, 1,7- and 1,1 2-dicarba-closo-dodecaboranes (phenylcarboranes) proceeded in the presence of trifluoromethanesulfonic acid. In spite of the strong electron-withdrawing effect of the carborane skeleton, para-acylated products predominated. However, substitution of a methyl group at the 2-position of 1-phenyl-1,2-carborane resulted in a change of isomer distribution. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：9073 / 9076

页数：4

共 18 条

[11]

Iijima T, 1999, CHEM PHARM BULL, V47, P398

[12]

KALININ VN, 1977, DOKL AKAD NAUK SSSR+, V236, P367

[13] GLYCOSYLCARBORANE DERIVATIVES AND THE DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF A DIASTEREOMERIC TRIOL FROM X-RAY-DIFFRACTION [J].

MAURER, JL ;

BERCHIER, F ;

SERINO, AJ ;

KNOBLER, CB ;

HAWTHORNE, MF .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :838-843

[14] STERIC EFFECTS IN HETEROBORANES .3. 1-PH-2-ME-1,2-CLOSO-C2B10H10 [J].

MCGRATH, TD ;

WELCH, AJ .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 :646-649

[15] INVOLVEMENT OF DICATIONIC SPECIES AS THE REACTIVE INTERMEDIATES IN GATTERMANN, HOUBEN-HOESCH, AND FRIEDEL-CRAFTS REACTIONS OF NONACTIVATED BENZENES [J].

SATO, Y ;

YATO, M ;

OHWADA, T ;

SAITO, S ;

SHUDO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3037-3043

[16] EFFECT OF SOLVENTS ON ELECTRONIC PROPERTIES OF 1-O-CARBORANYL, 3-O-CARBORANYL AND 1-M-CARBORANYL GROUPS [J].

ZAKHARKIN, LI ;

KALININ, VN ;

SNYAKIN, AP ;

KVASOV, BA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1969, 18 (01) :19-+

[17]

ZAKHARKIN LI, 1987, ZH ORG KHIM+, V23, P1691

[18]

ZAKHARKIN LI, 1974, IAN SSSR KH, P2632

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