COBALT(II)-CATALYZED REACTION BETWEEN POLYCYCLIC AROMATIC-ALDEHYDES AND ACETIC-ANHYDRIDE - FORMATION OF ACYLALS, NOT 1,2-DIKETONES

被引：22

作者：

FRY, AJ

RHO, AK

SHERMAN, LR

SHERWIN, CS

机构：

[1] Department of Chemistry, Wesleyan University, Middletown

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 10期

关键词：

D O I：

10.1021/jo00010a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several polycyclic aromatic aldehydes were found to react with acetic anhydride in acetonitrile in the presence of excess CoCl2 to afford the corresponding acylals [ArCH(OAc)2]. The results are not consistent with the literature report (Ahmad, S.; Iqbal, J. J. Chem. Soc., Chem. Commun. 1987, 692) that substituted benzaldehydes afford 1,2-diketones under similar conditions. The cobalt(II) chloride probably promotes acylal formation through its weakly Lewis acid character.

引用

收藏

页码：3283 / 3286

页数：4

相关论文

共 24 条

[1] COBALT(II) CHLORIDE CATALYZED COUPLING OF ACETIC-ANHYDRIDE WITH ALDEHYDES - A NOVEL SYNTHESIS OF ASYMMETRICAL 1,2-DIONES [J].

AHMAD, S ;

IQBAL, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (09) :692-693

[2] COBALT(II) CHLORIDE CATALYZED ACYLATIVE CLEAVAGE OF ETHERS [J].

AHMAD, S ;

IQBAL, J .

CHEMISTRY LETTERS, 1987, (05) :953-956

[3]

BERTHIER G, 1966, CHEM CARBONYL GROUP, V1, P1

[4] THE REACTION BETWEEN 7-OXANORBORNADIENES AND TETRAARYLCYCLOPENTADIENONES - A SHORT SYNTHESIS OF 1,2,3,4-TETRAARYLBENZENES [J].

FRY, AJ ;

SHERMAN, LR ;

BEAULIEU, AR ;

SHERWIN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :389-391

[5]

FRY AJ, 1989, SYNTHETIC ORGANIC EL, P96

[6] LANTHANOIDS IN ORGANIC SYNTHESES .7. SELECTIVE REDUCTIONS OF CARBONYL GROUPS IN AQUEOUS ETHANOL SOLUTION [J].

GEMAL, AL ;

LUCHE, JL .

TETRAHEDRON LETTERS, 1981, 22 (41) :4077-4080

[7]

GOMBERG M, 1929, J AM CHEM SOC, V51, P2238

[8] COBALT(II) CHLORIDE CATALYZED REGIOSELECTIVE CLEAVAGE OF OXIRANES WITH CHLOROTRIMETHYLSILANE [J].

IQBAL, J ;

KHAN, MA .

CHEMISTRY LETTERS, 1988, (07) :1157-1158

[9] PROTECTING GROUPS IN ORGANIC-SYNTHESIS .8. CONVERSION OF ALDEHYDES INTO GEMINAL DIACETATES [J].

KOCHHAR, KS ;

BAL, BS ;

DESHPANDE, RP ;

RAJADHYAKSHA, SN ;

PINNICK, HW .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (10) :1765-1767

[10] EFFICIENT SYNTHESIS OF ACETALS CATALYZED BY RARE-EARTH CHLORIDES [J].

LUCHE, JL ;

GEMAL, AL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (22) :976-977