DEPROTECTION OF ACETALS AND SILYL ETHERS BY DDQ - IS DDQ A NEUTRAL CATALYST

被引：51

作者：

OKU, A

KINUGASA, M

KAMADA, T

机构：

来源：

CHEMISTRY LETTERS | 1993年 / 01期

关键词：

D O I：

10.1246/cl.1993.165

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) in wet ethyl acetate at room temperature catalytically hydrolyzed acyclic acetals effectively and selectively among ethereal functional groups such as dioxoranes, 1,3-dioxanes, oxiranes, TMS- and TBDMS ethers. The mechanism is discussed on the basis of the function of DDQ as a Lewis acid in a wet solvent.

引用

收藏

页码：165 / 168

页数：4

相关论文

共 11 条

[1]

CHIHARA H, 1984, KIAGAKUBINRAN, V2, P203

[2] 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

[3] 2,3-DICHLORO-5,6-DICYANO-PARA-BENZOQUINONE, AN EFFICIENT, MILD, NEUTRAL AND HIGHLY REGIOSELECTIVE CATALYST FOR ALCOHOLYSIS OF EPOXIDES [J].

IRANPOOR, N ;

BALTORK, IM .

TETRAHEDRON LETTERS, 1990, 31 (05) :735-738

[4]

KAMADA T, 1991, 62ND NAT M CHEM SOC

[5]

KINUGASA M, 1992, 63RD NAT M CHEM SOC, P2272

[6] ELECTRON-TRANSFER PHOTOINDUCED CLEAVAGE OF ACETALS - A MILD PREPARATION OF ALKYL RADICALS [J].

MELLA, M ;

FASANI, E ;

ALBINI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :3051-3057

[7] KINETIC AND EQUILIBRIUM STUDIES OF CYCLIC KETAL FORMATION AND HYDROLYSIS [J].

NEWMAN, MS ;

HARPER, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (23) :6350-6355

[8]

OHTAKI H, 1984, KAGAKUBINRAN, V2, P339

[9]

OIKAWA Y, 1982, TETRAHEDRON LETT, V23, P3021

[10] GEM-DIALKYL EFFECT .2. A COMPARISON OF KINETIC AND EQUILIBRIUM APPROACHES TO SELECTIVE KETALIZATION OF 5ALPHA-ANDROSTANE-3,17-DIONE WITH VARIOUS GLYCOLS [J].

SMITH, SW ;

NEWMAN, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (05) :1249-&