Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

The scope of applications of dialkyl dicyanofumarates and maleates as highly functionalized electron-deficient dipolarophiles, dienophiles and Michael acceptors is summarized. The importance for the studies on reaction mechanisms of cycloadditions is demonstrated. Multistep reactions with 1,2-diamin...

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Main Authors: Grzegorz Mlostoń, Heinz Heimgartner
Format: Article
Language:English
Published: Beilstein-Institut 2017-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
cycloaddition reactions
electron-deficient ethenes
heterocyclization reactions
Michael additions
SET mechanism
Online Access:https://doi.org/10.3762/bjoc.13.221
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spelling doaj-8c9c6858beee423b856ba44b6e1128ec2021-02-02T03:26:46ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-10-011312235225110.3762/bjoc.13.2211860-5397-13-221Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studiesGrzegorz Mlostoń0Heinz Heimgartner1Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, PL 91-403 Łódż, PolandDepartment of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057, SwitzerlandThe scope of applications of dialkyl dicyanofumarates and maleates as highly functionalized electron-deficient dipolarophiles, dienophiles and Michael acceptors is summarized. The importance for the studies on reaction mechanisms of cycloadditions is demonstrated. Multistep reactions with 1,2-diamines and β-aminoalcohols leading to diverse five- and six-membered heterocycles are discussed. Applications of dialkyl dicyanofumarates as oxidizing agents in the syntheses of disulfides and diselenides are described. The reactions with metallocenes leading to charge-transfer complexes with magnetic properties are also presented.https://doi.org/10.3762/bjoc.13.221cycloaddition reactionselectron-deficient ethenesheterocyclization reactionsMichael additionsSET mechanism
collection DOAJ
language English
format Article
sources DOAJ
author Grzegorz Mlostoń
Heinz Heimgartner
spellingShingle Grzegorz Mlostoń
Heinz Heimgartner
Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
Beilstein Journal of Organic Chemistry
cycloaddition reactions
electron-deficient ethenes
heterocyclization reactions
Michael additions
SET mechanism
author_facet Grzegorz Mlostoń
Heinz Heimgartner
author_sort Grzegorz Mlostoń
title Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
title_short Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
title_full Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
title_fullStr Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
title_full_unstemmed Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
title_sort dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2017-10-01
description The scope of applications of dialkyl dicyanofumarates and maleates as highly functionalized electron-deficient dipolarophiles, dienophiles and Michael acceptors is summarized. The importance for the studies on reaction mechanisms of cycloadditions is demonstrated. Multistep reactions with 1,2-diamines and β-aminoalcohols leading to diverse five- and six-membered heterocycles are discussed. Applications of dialkyl dicyanofumarates as oxidizing agents in the syntheses of disulfides and diselenides are described. The reactions with metallocenes leading to charge-transfer complexes with magnetic properties are also presented.
topic cycloaddition reactions
electron-deficient ethenes
heterocyclization reactions
Michael additions
SET mechanism
url https://doi.org/10.3762/bjoc.13.221
work_keys_str_mv AT grzegorzmloston dialkyldicyanofumaratesanddicyanomaleatesasversatilebuildingblocksforsyntheticorganicchemistryandmechanisticstudies
AT heinzheimgartner dialkyldicyanofumaratesanddicyanomaleatesasversatilebuildingblocksforsyntheticorganicchemistryandmechanisticstudies
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