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An unexpected reaction of diethyl phosphite with electron-deficient dialkyl dicyanofumarates


Mloston, Grzegorz; Celeda, Malgorzata; Heimgartner, Heinz (2016). An unexpected reaction of diethyl phosphite with electron-deficient dialkyl dicyanofumarates. Phosphorus, Sulfur, and Silicon and the Related Elements, 191(2):207-210.

Abstract

Diethyl phosphite reacts with both dimethyl dicyanofumarate and dicyanomaleate in boiling 1,2-dichloroethane to yield, after chromatographic workup, a 1:1-mixture of the corresponding meso- and dl-dicyanosuccinates. The analogous transformation was observed in the cases of diethyl and diisopropyl dicyanofumarates. A reaction pathway via initial formation of a P–C bond followed by its hydrolytic cleavage is proposed.

Abstract

Diethyl phosphite reacts with both dimethyl dicyanofumarate and dicyanomaleate in boiling 1,2-dichloroethane to yield, after chromatographic workup, a 1:1-mixture of the corresponding meso- and dl-dicyanosuccinates. The analogous transformation was observed in the cases of diethyl and diisopropyl dicyanofumarates. A reaction pathway via initial formation of a P–C bond followed by its hydrolytic cleavage is proposed.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Addition reactions; reaction mechanisms; electron deficient alkenes; dialkyl phosphites; Michael addition
Language:English
Date:February 2016
Deposited On:23 Nov 2015 11:27
Last Modified:04 Nov 2016 01:00
Publisher:Taylor & Francis
ISSN:1026-7719
Funders:University of Lodz
Publisher DOI:https://doi.org/10.1080/10426507.2015.1085045

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