Fluorinative Beckmann fragmentation: Fluorinative alpha-cleavage of cyclicketoximes by diethylaminosulfur trifluoride

Authors
Kirihara, M Niimi, K Okumura, M Momose, T
Citation
M. Kirihara et al., Fluorinative Beckmann fragmentation: Fluorinative alpha-cleavage of cyclicketoximes by diethylaminosulfur trifluoride, CHEM PHARM, 48(2), 2000, pp. 220-222
Citations number
19
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
48
Issue
2
Year of publication
2000
Pages
220 - 222
Database
ISI
SICI code
0009-2363(200002)48:2<220:FBFFAO>2.0.ZU;2-2
Abstract
Diethylaminosulfur trifluoride reacted with cyclic ketoximes bearing substi tuent(s) that can stabilize a carbocation to cause fluorinative fragmentati on, affording fluorinated carbonitrile. Ketoximes lacking such substituents afforded complex mixtures. However. the introduction of a sulfur functiona lity, which can stabilize a carbocation and can be easily removed from the reaction products, into the ketoxime nas effective for producing the fluori native fragmentation.