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Search for "substitution reaction" in Full Text gives 139 result(s) in Beilstein Journal of Organic Chemistry.

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated SNAr reaction

  • Charlotte Wiles and
  • Paul Watts

Beilstein J. Org. Chem. 2011, 7, 1360–1371, doi:10.3762/bjoc.7.160

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  • respectively) in dimethylacetamide (DMA) and the second 1,8-diazabicycloundec-7-ene (DBU, 6, 1.95 M) in DMA, we investigated the nucleophilic substitution reaction under flow conditions. By using a reaction time of 10 min, achieved by setting a total flow rate of 1 µL·min−1, the effect of reactor temperature
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Published 04 Oct 2011

Gold-catalyzed propargylic substitutions: Scope and synthetic developments

  • Olivier Debleds,
  • Eric Gayon,
  • Emmanuel Vrancken and
  • Jean-Marc Campagne

Beilstein J. Org. Chem. 2011, 7, 866–877, doi:10.3762/bjoc.7.99

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  • catalyst loading to 1 mol %, the substitution product 10 could be isolated in 60% yield (along with 35% of the Meyer–Schuster product 11). This result could be explained by considering that 11 is derived from 10 through the conjugated addition of water (residual or produced during the substitution reaction
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Review
Published 28 Jun 2011

Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

  • Haruo Aikawa,
  • Tetsuro Kaneko,
  • Naoki Asao and
  • Yoshinori Yamamoto

Beilstein J. Org. Chem. 2011, 7, 648–652, doi:10.3762/bjoc.7.76

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  • -induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure. Keywords: alkylation; gold catalysis; leaving group; silyl enol ether; substitution reaction
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Letter
Published 20 May 2011

Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

  • Bernhard Gutmann,
  • Toma N. Glasnov,
  • Tahseen Razzaq,
  • Walter Goessler,
  • Dominique M. Roberge and
  • C. Oliver Kappe

Beilstein J. Org. Chem. 2011, 7, 503–517, doi:10.3762/bjoc.7.59

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  • in a 3 μL fused-silica capillary, albeit not under continuous flow conditions, is the nucleophilic aromatic substitution reaction of 4-fluoro-1-nitrobenzene (15) with pyrrolidine (16) in THF (ΔV≠ = −58 cm3/mol) (Scheme 5) [71]. In order to confirm that these pressure enhancements can also be
  • , significant corrosion of the reactor material can result, leading to unwanted side reactions. In addition, in specific cases reaction pressure can influence reaction rates as evidenced by the nucleophilic aromatic substitution reaction of 1-fluoro-4-nitrobenzene with pyrrolidine in the 60–180 bar pressure
  • experienced in a stainless steel mesofluidic flow reactor, the nucleophilic substitution was repeated in an X-Cube Flash instrument. Employing an 8 mL steel coil and an overall flow rate of 1 mL/min (two individual reagent streams at 0.5 mL/min each, residence time = 8 min), the conversion of the substitution
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Published 21 Apr 2011

Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study

  • Benan Kilbas and
  • Metin Balci

Beilstein J. Org. Chem. 2011, 7, 246–253, doi:10.3762/bjoc.7.33

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  • SN2' substitution reaction mechanism [27][28][29][30], nucleophiles attack the double bond from the same side from which the leaving group departs, as shown below (Figure 3). Therefore, we assume that metal is bonded to the allylic system from the same side as the nucleophile attacking the double bond
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Published 24 Feb 2011

SbCl3-catalyzed one-pot synthesis of 4,4′-diaminotriarylmethanes under solvent-free conditions: Synthesis, characterization, and DFT studies

  • Ghasem Rezanejade Bardajee

Beilstein J. Org. Chem. 2011, 7, 135–144, doi:10.3762/bjoc.7.19

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  • the reaction can be summarized as a tandem regioselective electrophilic aromatic substitution reaction of N,N-dimethylaniline and aldehydes, in which SbCl3 (as a Lewis acid catalyst) activates the carbonyl group of the aldehydes. If we accept this mechanism, one can expect a general influence of
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Published 31 Jan 2011

Catalysis: transition-state molecular recognition?

  • Ian H. Williams

Beilstein J. Org. Chem. 2010, 6, 1026–1034, doi:10.3762/bjoc.6.117

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  • coordinates for nucleophilic substitution and proton transfer from Glu172, showed no requirement for protonation of the activated nucleofuge [24]. PMFs, with respect to the nucleophilic substitution reaction coordinate for both the wild-type and the Tyr69Phe mutant, computed with the same QM/MM MD method
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Commentary
Published 03 Nov 2010

Chromo- and fluorophoric water-soluble polymers and silica particles by nucleophilic substitution reaction of poly(vinyl amine)

  • Katja Hofmann,
  • Ingolf Kahle,
  • Frank Simon and
  • Stefan Spange

Beilstein J. Org. Chem. 2010, 6, No. 79, doi:10.3762/bjoc.6.79

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Published 22 Jul 2010

A short and efficient synthesis of valsartan via a Negishi reaction

  • Samir Ghosh,
  • A. Sanjeev Kumar and
  • G. N. Mehta

Beilstein J. Org. Chem. 2010, 6, No. 27, doi:10.3762/bjoc.6.27

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  • could be obtained from commercially available benzonitrile. Aryl bromide 5 could be accessed by several discrete reactions of compound 3 and compound 4 via a nucleophilic substitution reaction. As shown in Scheme 2, inexpensive and commercially readily available valeryl chloride 1 was coupled with L
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Published 18 Mar 2010

The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts

  • Kari Raatikainen,
  • Massimo Cametti and
  • Kari Rissanen

Beilstein J. Org. Chem. 2010, 6, No. 4, doi:10.3762/bjoc.6.4

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  • nucleophilic substitution reaction of 3-iodopyridine with (chloromethyl)benzene (the synthesic details will be reported elsewhere). Slow evaporation of a moist ethanol solution gave an X-ray-quality crystal of 9. The asymmetric unit contains two molecules of N-benzyl-3-iodopyridinium chloride, a water molecule
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Published 15 Jan 2010

The vicinal difluoro motif: The synthesis and conformation of erythro- and threo- diastereoisomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives

  • David O'Hagan,
  • Henry S. Rzepa,
  • Martin Schüler and
  • Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2006, 2, No. 19, doi:10.1186/1860-5397-2-19

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  • acetonitrile in the dark. Under these conditions, the substitution proceeds smoothly to erythro-13 but only in 56% de indicating a significant loss of stereochemical control during the reaction. The predominant stereochemical outcome of the fluorine substitution reaction suggests a double inversion mechanism
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Published 02 Oct 2006

EcoScale, a semi- quantitative tool to select an organic preparation based on economical and ecological parameters

  • Koen Van Aken,
  • Lucjan Strekowski and
  • Luc Patiny

Beilstein J. Org. Chem. 2006, 2, No. 3, doi:10.1186/1860-5397-2-3

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  • involved. It takes into account the amount of the reagents incorporated into the end product. Cycloadditions are examples of transformations with 100% atom economy. For other reactions (e.g. substitution reaction), a 100 % economy can never be reached due to the intrinsic nature of the reaction. The main
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Published 03 Mar 2006

New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline- 2,4(1H,3H)-dione compounds

  • Oldřich Paleta,
  • Karel Pomeisl,
  • Stanislav Kafka,
  • Antonín Klásek and
  • Vladislav Kubelka

Beilstein J. Org. Chem. 2005, 1, No. 17, doi:10.1186/1860-5397-1-17

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  • out[3] (product 2) via the intramolecular Wittig synthesis using a bromoacetyl derivative of the starting 3-hydroxyquinolinediones (1, Scheme 1). Unlike haloalkanes and halocycloalkanes that undergo nucleophilic substitution reaction with trialkyl phosphites to afford the corresponding phosphonates
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Preliminary Communication
Published 09 Dec 2005
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  • structural complexity had been introduced as a consequence of the two-directional nature of the approach (sulfonamide oxidation, two oxidative ring expansions, two protection reactions and one N,O acetal substitution reaction). The stage was set for two-directional functionalisation of the heterocyclic rings
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Published 26 Aug 2005
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