A straight synthesis of 2-(alpha-substituted N-tosylaminomethyl)-2,5-dihydrofurans by the reaction of N-sulfonylimines with arsonium 4-hydroxyl-cis-2-butenylides

Authors
Li, AH Deng, WP Dai, LX Hou, XL
Citation
Ah. Li et al., A straight synthesis of 2-(alpha-substituted N-tosylaminomethyl)-2,5-dihydrofurans by the reaction of N-sulfonylimines with arsonium 4-hydroxyl-cis-2-butenylides, CHIN J CHEM, 17(3), 1999, pp. 300-304
Citations number
21
Categorie Soggetti
Chemistry
Journal title
CHINESE JOURNAL OF CHEMISTRY
ISSN journal
1001604X → ACNP
Volume
17
Issue
3
Year of publication
1999
Pages
300 - 304
Database
ISI
SICI code
1001-604X(199905)17:3<300:ASSO2N>2.0.ZU;2-8
Abstract
On treatment of N-tosylimines (1) and 4-hydroxyl-cis-butenyl arsonium salt (5) with KOH in acetonitrile at room temperature, 2-(alpha-substituted N-to sylaminomethyl)-2,5-dihydrofurans (4) were obtained in moderate yields. The arsonium salt (5) acts formally as an equivalent of 2,5-dihydrofuran synon . A plausible mechanism was proposed for this new 5-membered cyclization re action.