Literature DB >> 18763839

Dearomatization reactions of aryl-substituted silaaziridines.

Zulimar Nevárez1, K A Woerpel.   

Abstract

Silaaziridines with an aryl group on either the carbon or the nitrogen atom undergo dearomatization reactions upon treatment with benzaldehyde. The reactions form new bonds ortho to the nitrogen substituents with high diastereoselectivity. These dearomatization processes likely are driven by relief of the considerable ring strain of the silaaziridine.

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Year:  2008        PMID： 18763839      PMCID： PMC2664301          DOI： 10.1021/jo801502x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

1.  Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis.

Authors:  Hans-Ulrich Reissig; Reinhold Zimmer
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  A comparison of the Cope rearrangements of cis-1,2-divinylcyclopropane, cis-2,3-divinylaziridine, cis-2,3-divinyloxirane, cis-2,3-divinylphosphirane, and cis-2,3-divinylthiirane: a DFT study.

Authors:  Metin Zora
Journal:  J Org Chem       Date:  2005-07-22       Impact factor: 4.354

3.  The profound effect of fluorine substitution on the reactivity and regioselectivity of nucleophilic substitution reactions of strained heterocycles. A study of aziridine and its derivatives.

Authors:  Harold D Banks
Journal:  J Org Chem       Date:  2006-10-13       Impact factor: 4.354

4.  Metal-catalyzed silylene transfer to imines: synthesis and reactivity of silaaziridines.

Authors:  Zulimar Nevárez; K A Woerpel
Journal:  Org Lett       Date:  2007-08-22       Impact factor: 6.005

Review 5.  Aziridines: epoxides' ugly cousins?

Authors:  J B Sweeney
Journal:  Chem Soc Rev       Date:  2002-09       Impact factor: 54.564

6.  Cyclopropanation with Fischer acyloxycarbene complexes: preparation of cyclopropane and cycloheptane-fused gamma-lactones.

Authors:  Jose Barluenga; Fernando Aznar; Ignacio Gutiérrez; J Alfredo Martín
Journal:  Org Lett       Date:  2002-08-08       Impact factor: 6.005

7.  ZnBr2 -Catalyzed Insertions of Carbonyl Compounds into Silacyclopropanes: Regiochemical Reversal Dependent on Metal Salt.

Authors:  Annaliese K Franz; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2000-12-01       Impact factor: 15.336
  7 in total
  1 in total

1.  Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones.

Authors:  Heloise Brice; Jonathan Clayden; Stuart D Hamilton
Journal:  Beilstein J Org Chem       Date:  2010-03-02       Impact factor: 2.883
  1 in total

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