INTRAMOLECULAR OXIDATIVE COUPLING OF AROMATIC-COMPOUNDS .5. PARA PARA DIPHENOLIC OXIDATIVE COUPLING AS A POSSIBLE ROUTE TO THE EUPODIENONE SKELETON

被引：6

作者：

CARROLL, AR

KRAUSS, AS

TAYLOR, WC

机构：

[1] Department of Organic Chemistry, University of Sydney, NSW

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1993年 / 46卷 / 03期

关键词：

D O I：

10.1071/CH9930277

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of (2RS,3RS)-1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (9) is described. Diphenolic oxidative coupling of (9) gave the unstable dienone (24), which decomposed in methanol to give what is believed to be the acetal (26). Synthesis of the related diarylbutane (10) was also achieved, but diphenolic coupling gave no useful result. The claimed formation of the bis(spiro dienone) (7) on oxidation of 4,4'-(butane-1,4-diyl)bisphenol could not be confirmed.

引用

收藏

页码：277 / 292

页数：16

相关论文

共 15 条

[1] PREPARATION AND SOLVOLYSIS OF DISPIROTETRAENEDIONES [J].

AFZAL, MN ;

ALLBUTT, AD ;

JORDAAN, A ;

KIRBY, GW .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (17) :996-&

[2] SYNTHESIS OF AN ISOSTEGANE FROM MATAIRESINOL [J].

CAMBIE, RC ;

DUNLOP, MG ;

RUTLEDGE, PS ;

WOODGATE, PD .

SYNTHETIC COMMUNICATIONS, 1980, 10 (11) :827-831

[3] A CONVENIENT REAGENT FOR THE INTERMOLECULAR COUPLING OF ALDEHYDES AND KETONES TO FORM OLEFINS [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (08) :1439-1443

[4] NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].

COREY, EJ ;

DANHEISER, RL ;

CHANDRASEKARAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265

[5] DERIVATIVES OF ORTHOACIDS .2. PREPARATION OF OLEFINS FROM 1,2-DIOLS [J].

CRANK, G ;

EASTWOOD, FW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (12) :1392-&

[6]

FORREST DA, 1973, J CHEM SOC P1, P2388

[7] THE PREPARATION OF ALPHA,OMEGA-BIS-PARA-ANISYLALKANES [J].

KADKHODAYAN, M ;

SINGLETON, T ;

HELDRICH, FJ .

SYNTHETIC COMMUNICATIONS, 1984, 14 (08) :707-712

[8] INTRAMOLECULAR OXIDATIVE COUPLING OF AROMATIC-COMPOUNDS .1. OXIDATION OF DIPHENOLIC SUBSTRATES [J].

KRAUSS, AS ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (09) :1307-1333

[9] INTRAMOLECULAR OXIDATIVE COUPLING OF AROMATIC-COMPOUNDS .4. OXIDATION OF NONPHENOLIC SUBSTRATES [J].

KRAUSS, AS ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (05) :935-939

[10] MECHANISTIC ASPECTS OF REARRANGEMENT AND ELIMINATION REACTIONS OF ALPHA-METALATED BENZYL ALKYL ETHERS [J].

LANSBURY, PT ;

PATTISON, VA ;

SIDLER, JD ;

BIEBER, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (01) :78-&