Collect. Czech. Chem. Commun.
2009, 74, 335-346
https://doi.org/10.1135/cccc2008095
Published online 2009-02-18 14:57:55
Reactions of β-aminovinyl bromodifluoromethyl ketones with alkyl phosphites: Perkow versus Arbuzov
Karen V. Tarasenkoa, Igor I. Gerusa,*, Valery P. Kukhara and Vitaly V. Polovinkob
a Department of Fine Organic Synthesis, Institute of Bioorganic Chemistry and Petrochemistry, National Ukrainian Academy of Science, Murmanskaya Str. 1, Kiev, 02094, Ukraine
b Enamine Ltd., A. Matrosova Str. 23, Kiev, 01103, Ukraine
Abstract
New bromodifluoromethyl enaminones 1a–1f and γ-bromo-β-morpholinopropenyl fluoromethyl ketones 2a, 2b were synthesized. N-Substituted bromodifluoromethyl enaminones 1a–1d do not react with triethyl or diethyl phosphites, whereas N-acylated enaminones 1e, 1f gave difluorodienyl phosphates 4a, 4b as Perkow rearrangement products. Fluoroketone 2a reacts easily with triethyl phosphite according to the Arbuzov protocol and a perspective building block – trifluoromethyl-containing phosphonate 7a is formed.
Keywords: Fluorine; Enaminones; Perkow reaction; Phosphates; Arbuzov reaction; Phosphonates; Fluorinated ketones; Enol phosphates.
References: 21 live references.
