SYNTHESES OF DIALKYL AND FUNCTIONALIZED KETONES VIA 1-(BENZOTRIAZOL-1-YL)ALKYL METHYL THIOETHERS

Authors
KATRITZKY AR ONICIU DC GHIVIRIGA I SOTI F
Citation
Ar. Katritzky et al., SYNTHESES OF DIALKYL AND FUNCTIONALIZED KETONES VIA 1-(BENZOTRIAZOL-1-YL)ALKYL METHYL THIOETHERS, Journal of organic chemistry, 63(7), 1998, pp. 2110-2115
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
7
Year of publication
1998
Pages
2110 - 2115
Database
ISI
SICI code
0022-3263(1998)63:7<2110:SODAFK>2.0.ZU;2-G
Abstract
Benzotriazol-1-ylmethyl methyl thioether (1), after easy deprotonation by BuLi, reacted with alkyl halides to afford 1-(benzotriazol-1-yl)al kyl methyl thioethers 2 in good yields. The utility of compounds 2 as alkanoyl anion equivalents was demonstrated by the reactions of their anions with alkyl halides, aldehydes, ketones, esters, and phenyl isoc yanate: the products were readily hydrolyzed to alpha-functionalized k etones in dilute aqueous acid.