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Dialkyl dicyanofumarates as oxidizing reagents for the conversion of thiols into disulfides and selenols into diselenides


Mloston, Grzegorz; Capperucci, Antonella; Tanini, Damiano; Hamera-Faldyga, Roza; Heimgartner, Heinz (2017). Dialkyl dicyanofumarates as oxidizing reagents for the conversion of thiols into disulfides and selenols into diselenides. European Journal of Organic Chemistry, 2017(46):6831-6839.

Abstract

Aliphatic and aromatic thiols react smoothly with dialkyl dicyanofumarates in CH2Cl2 at room temperature to give the corresponding disulfides in excellent yields. Aliphatic 1,2-, 1,3-, and 1,4-dithiols afford cyclic disulfides. Analogous reaction courses were observed starting with selenols, and the required diselenides were also formed in nearly quantitative yields. In all of the reactions, dialkyl dicyanosuccinates formed as a 1:1-mixture of diastereoisomers as the only other product. Cysteamine (2-mercaptoethylamine) behaved differently; the Michael addition of the primary amine group led to complete consumption of the dicyanofumarate, and the formation of the disulfide containing the enamine moiety occurred without the formation of dicyanosuccinate.

Abstract

Aliphatic and aromatic thiols react smoothly with dialkyl dicyanofumarates in CH2Cl2 at room temperature to give the corresponding disulfides in excellent yields. Aliphatic 1,2-, 1,3-, and 1,4-dithiols afford cyclic disulfides. Analogous reaction courses were observed starting with selenols, and the required diselenides were also formed in nearly quantitative yields. In all of the reactions, dialkyl dicyanosuccinates formed as a 1:1-mixture of diastereoisomers as the only other product. Cysteamine (2-mercaptoethylamine) behaved differently; the Michael addition of the primary amine group led to complete consumption of the dicyanofumarate, and the formation of the disulfide containing the enamine moiety occurred without the formation of dicyanosuccinate.

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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:Physical and Theoretical Chemistry, Organic Chemistry
Language:English
Date:September 2017
Deposited On:13 Nov 2017 16:29
Last Modified:05 Sep 2018 00:00
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1099-0690
Funders:National Science Center (Cracow, Poland), Maestro-3 Project (Grant no. Dec-2012/06/A/ST5/00219
Additional Information:This is the peer reviewed version of the following article: Mlostoń, G., Capperucci, A., Tanini, D., Hamera-Fałdyga, R. and Heimgartner, H. (2017), Dialkyl Dicyanofumarates as Oxidizing Reagents for the Conversion of Thiols into Disulfides and Selenols into Diselenides. Eur. J. Org. Chem.., which has been published in final form at 10.1002/ejoc.201701066. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving (http://olabout.wiley.com/WileyCDA/Section/id-820227.html#terms).
OA Status:Green
Publisher DOI:https://doi.org/10.1002/ejoc.201701066

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