Unexpected cycloreversion of a tosylated sugar oxetane under E2 conditions.: The facile formation of 2-(2-furanyl)-1,3-dioxolane from a novel 2,5:4,6-dianhydro-L-idose derivative

被引：2

作者：

Popsavin, V ^{[1
]}

Radic, L ^{[1
]}

Popsavin, M ^{[1
]}

Cirin-Novta, V ^{[1
]}

机构：

[1] Univ Novi Sad, Fac Sci, Dept Chem, YU-21000 Novi Sad, Serbia And Mont, Serbia

来源：

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY | 2004年 / 69卷 / 02期

关键词：

2,5-anhydro-L-idose; 2,5 : 4,6-dianhydro-L-idose; sugar oxetanes; cycloreversion;

D O I：

10.2298/JSC0402117P

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2.5:4.6-Dianhydro-3-O-p-toluensulfonyl-L-idose ethylene acetal (4) was synthesized with the aim of studying is, chemical behaviour in the presence of several basic agents (Bu4NF/MeCN. NaOMe/MeOH, KOBt/(BuOH)-O-t/THF, and NaH/DMSO). Treatment of 4 with sodium hydride in dimethyl sulphoxide at room temperature unexpectedly gave the 2-(2-furanyl)- 1,3-dioxolane. The mechanism of the process presumably involved the initial conversion of 4 to the corresponding 2,3-unsaturated derivative 5, followed by a facile oxetane ring cycloreversion by the elimination of formaldehyde.

引用

页码：117 / 122

页数：6