Reactions of β-aminovinyl bromodifluoromethyl ketones with alkyl phosphites: Perkow versus Arbuzov

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Title:Reactions of β-aminovinyl bromodifluoromethyl ketones with alkyl phosphites: Perkow versus Arbuzov
Creators:
Tarasenko, Karen V.
Gerus, Igor I.
Kukhar, Valery P.
Polovinko, Vitaly V.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 74, 2, pp. 335-346
Uncontrolled Keywords:Fluorine, Phosphates, Phosphonates, Perkow reaction, Enaminones, Arbuzov reaction, Fluorinated ketones, Enol phosphates

Abstract

New bromodifluoromethyl enaminones <b>1a</b>–<b>1f</b> and γ-bromo-β-morpholinopropenyl fluoromethyl ketones <b>2a</b>, <b>2b</b> were synthesized. <i>N</i>-Substituted bromodifluoromethyl enaminones <b>1a</b>–<b>1d</b> do not react with triethyl or diethyl phosphites, whereas <i>N</i>-acylated enaminones <b>1e</b>, <b>1f</b> gave difluorodienyl phosphates <b>4a</b>, <b>4b</b> as Perkow rearrangement products. Fluoroketone <b>2a</b> reacts easily with triethyl phosphite according to the Arbuzov protocol and a perspective building block – trifluoromethyl-containing phosphonate <b>7a</b> is formed.

Title:Reactions of β-aminovinyl bromodifluoromethyl ketones with alkyl phosphites: Perkow versus Arbuzov
Creators:
Tarasenko, Karen V.
Gerus, Igor I.
Kukhar, Valery P.
Polovinko, Vitaly V.
Uncontrolled Keywords:Fluorine, Phosphates, Phosphonates, Perkow reaction, Enaminones, Arbuzov reaction, Fluorinated ketones, Enol phosphates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:74
Number:2
Page Range:pp. 335-346
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2008095UNSPECIFIED
ID Code:4102
Item Type:Article
Deposited On:02 Mar 2009 10:34
Last Modified:02 Mar 2009 09:34

Citation

Tarasenko, Karen V.; Gerus, Igor I.; Kukhar, Valery P.; Polovinko, Vitaly V. (2009) Reactions of β-aminovinyl bromodifluoromethyl ketones with alkyl phosphites: Perkow versus Arbuzov. Collection of Czechoslovak Chemical Communications, 74 (2). pp. 335-346. ISSN 0010-0765

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