REARRANGEMENT OF 2-(HALOALKOXY)PYRIDINES TO N-HALOALKYL-2(1H)-PYRIDONES

Authors
SCHMIDHAUSER JC KHOURI FF
Citation
Jc. Schmidhauser et Ff. Khouri, REARRANGEMENT OF 2-(HALOALKOXY)PYRIDINES TO N-HALOALKYL-2(1H)-PYRIDONES, Tetrahedron letters, 34(42), 1993, pp. 6685-6688
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
42
Year of publication
1993
Pages
6685 - 6688
Database
ISI
SICI code
0040-4039(1993)34:42<6685:RO2TN>2.0.ZU;2-N
Abstract
2-(Haloalkoxy)pyridines thermally rearrange to N-haloalkyl-2(1H)-pyrid ones in high Yield. The reaction rate is accelerated by use of a more polar solvent, by bromine rather than chlorine as the halogen substitu ent and by a two-carbon alkoxy chain as opposed to a three or, especia lly, four-carbon chain. The reaction kinetics can be interpreted in te rms of an oxazolium ion intermediate.