SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS BY THE ACID-CATALYZED DECOMPOSITION OF 1,2-DIOXAN-3-OLS

被引：24

作者：

QIAN, CY ^{[1
]}

HIROSE, J ^{[1
]}

NISHINO, H ^{[1
]}

KUROSAWA, K ^{[1
]}

机构：

[1] KUMAMOTO UNIV,FAC SCI,DEPT CHEM,KUMAMOTO 860,JAPAN

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1994年 / 31卷 / 05期

关键词：

D O I：

10.1002/jhet.5570310519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thirteen new 2,3,5-trisubstituted furans were prepared by the acid-catalyzed decomposition of 6,6-disubstituted 1,2-dioxan-3-ols in 57-93% yields. The reaction could be accounted for as the consequence of an oxygen-oxygen bond cleavage by acid and the migration of a phenyl group at the C-6 position followed by cyclization and elimination of a phenol. The migratory aptitude was in the order of 4-MeOC6H4- > 4-MeC6H4- > Ph- = 4-FC6H4- > 4-ClC6H4- = 4-BrC6H4- that was found from the competitive phenyl migration in the reaction of 1,2-dioxan-3-ols bearing two different substituents at the C-6 position.

引用

页码：1219 / 1227

页数：9

共 20 条

[1] ACID-CATALYZED REARRANGEMENT OF HYDROPEROXIDES .2. PHENYLCYCLOALKYL HYDROPEROXIDES [J].