MIXED QUINONE MONOKETALS VIA IODOBENZENE DIACETATE OXIDATION

被引：42

作者：

FLECK, AE ^{[1
]}

HOBART, JA ^{[1
]}

MORROW, GW ^{[1
]}

机构：

[1] UNIV DAYTON,DEPT CHEM,300 COLL PK,DAYTON,OH 45469

来源：

SYNTHETIC COMMUNICATIONS | 1992年 / 22卷 / 01期

关键词：

D O I：

10.1080/00397919208021090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of p-methoxyphenol, 4-methoxynaphthol and 4-acetamidophenol with iodobenzenediacetate in various alcohols as solvent afforded the corresponding mixed quinone or naphthoquinone monoketals in good yield. Oxidation of p-methoxyphenol in the presence of sorbyl alcohol led to in situ intramolecular Diels-Alder reactions proceeding by way of the corresponding mixed quinone monoketal.

引用

页码：179 / 187

页数：9

共 9 条

[1] CONJUGATE REDUCTION OF QUINONE DERIVATIVES - A ROUTE TO PHENOL KETO-TAUTOMER EQUIVALENTS
DOTY, BJ
MORROW, GW
[J]. TETRAHEDRON LETTERS, 1990, 31 (43) : 6125 - 6128
[2] HENTON DR, 1980, J ORG CHEM, V45, P3422, DOI 10.1021/jo01305a010
[3] HYPERVALENT IODINE OXIDATION OF N-ACYLTYRAMINES - SYNTHESIS OF QUINOL ETHERS, SPIROHEXADIENONES, AND HEXAHYDROINDOL-6-ONES
KITA, Y
TOHMA, H
KIKUCHI, K
INAGAKI, M
YAKURA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 435 - 438
[4] HYDROLYSIS OF N-ACETYL-PARA-BENZOQUINONE IMINES - PH-DEPENDENCE OF THE PARTITIONING OF A TETRAHEDRAL INTERMEDIATE
NOVAK, M
BONHAM, GA
MULERO, JJ
PELECANOU, M
ZEMIS, JN
BUCCIGROSS, JM
WILSON, TC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4447 - 4456
[5] PHENOLIC OXIDATION WITH (DIACETOXYIODO)BENZENE
PELTER, A
ELGENDY, S
[J]. TETRAHEDRON LETTERS, 1988, 29 (06) : 677 - 680
[6] SYNTHESES VIA ANODICALLY PRODUCED PHENOXENIUM IONS - APPLICATIONS IN THE FIELD OF PEPTIDES AND CARBOHYDRATES
RIEKER, A
BEISSWENGER, R
REGIER, K
[J]. TETRAHEDRON, 1991, 47 (4-5) : 645 - 654
[7] MIXED METHYL SILYL KETALS OF QUINONES - THEIR PREPARATION VIA ANODIC-OXIDATION AND THEIR CHEMISTRY
STERN, A
SWENTON, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2763 - 2768
[8] Swenton J. S., 1988, CHEM QUINONOID COM 2, V2, P899
[9] HYPERVALENT IODINE OXIDATION OF PARA-ALKOXYPHENOLS AND RELATED-COMPOUNDS - A GENERAL-ROUTE TO PARA-BENZOQUINONE MONOACETALS AND SPIRO LACTONES
TAMURA, Y
YAKURA, T
HARUTA, J
KITA, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) : 3927 - 3930

← 1 →