Cyanoacetylene and its derivatives: XXVI. Hydrohalogenation of 4-alkyl-4-hydroxy-2-alkynenitriles

Authors
Mal'kina, AG Nosyreva, VV Kudyakova, RN Sokolyanskaya, LV Trofimov, BA
Citation
Ag. Mal'Kina et al., Cyanoacetylene and its derivatives: XXVI. Hydrohalogenation of 4-alkyl-4-hydroxy-2-alkynenitriles, RUSS J ORG, 37(5), 2001, pp. 649-654
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
10704280 → ACNP
Volume
37
Issue
5
Year of publication
2001
Pages
649 - 654
Database
ISI
SICI code
1070-4280(200105)37:5<649:CAIDXH>2.0.ZU;2-R
Abstract
The reaction of 4-alkyl-4-hydroxy-2-alkynenitrites with hydrogen halides (H Cl and HI) in dioxane is accompanied by intramolecular cyclization with for mation of 5,5-dialkyl-4-halo-2-imino-2,5-dihydrofuran hydrohalides. Treatme nt of the latter with K2CO3 in ethanol yields 5,5-dialkyl-4-halo-2-imino-2, 5-diliydrofurans.