NDLI: Regio- and Stereoselectivity in the Decatungstate Photocatalyzed Alkylation of Alkenes by Alkylcyclohexanes

Please wait, while we are loading the content...

Year: 2017 Volume: 23

Year: 2016 Volume: 22

Year: 2015 Volume: 21

Year: 2014 Volume: 20

Year: 2013 Volume: 19

Year: 2012 Volume: 18

Year: 2011 Volume: 17

Year: 2010 Volume: 16

Year: 2009 Volume: 15

Year: 2009 Volume: 15 Issue: 48

Year: 2009 Volume: 15 Issue: 47

Year: 2009 Volume: 15 Issue: 46

Year: 2009 Volume: 15 Issue: 45

Year: 2009 Volume: 15 Issue: 44

Year: 2009 Volume: 15 Issue: 43

Year: 2009 Volume: 15 Issue: 42

Year: 2009 Volume: 15 Issue: 41

Year: 2009 Volume: 15 Issue: 40

Year: 2009 Volume: 15 Issue: 39

Year: 2009 Volume: 15 Issue: 38

Year: 2009 Volume: 15 Issue: 37

Year: 2009 Volume: 15 Issue: 36

Year: 2009 Volume: 15 Issue: 35

Year: 2009 Volume: 15 Issue: 34

Year: 2009 Volume: 15 Issue: 33

Year: 2009 Volume: 15 Issue: 32

Asymmetric iminium ion catalysis with a novel bifunctional primary amine thiourea: controlling adjacent quaternary and tertiary stereocenters.

Mechanistic Study of the Palladium–Phenanthroline Catalyzed Carbonylation of Nitroarenes and Amines: Palladium–Carbonyl Intermediates and Bifunctional Effects

Adducts between Dansylated Poly(propylene amine) Dendrimers and Anthracene Clips Mediated by $Zn^{II}$ Ions: Highly Efficient Photoinduced Energy Transfer

Determination of the Catalytic Pathway of a Manganese Arginase Enzyme Through Density Functional Investigation

Preparation and Characterisation of a New Inclusion Compound of Cucurbit[8]uril with a Nitroxide Radical

Diastereoselective, One-Pot Synthesis of Polyfunctionalized Bicyclo[3.3.1]nonanes by an Anionic Domino Process

Nanofibers from Oxazolidi-2-one Containing Hybrid Foldamers: What is the Right Molecular Size?

Michael Additions versus Cycloaddition Condensations with Ethyl Nitroacetate and Electron-Deficient Olefins

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using $Pt^{II}$ Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

Predicting the NMR Spectra of Paramagnetic Molecules by DFT: Application to Organic Free Radicals and Transition-Metal Complexes

Guanosine Hydrogen-Bonded Scaffolds: A New Way to Control the Bottom-Up Realisation of Well-Defined Nanoarchitectures

Palladium/Norbornene-Catalyzed Synthesis of Heteroatom-Containing o-Teraryls from Aryl Iodides and Heteroarenes through Double CH Activation in Sequence

Bifunctional Catalysis by Natural Cinchona Alkaloids: A Mechanism Explained

Polyamine Receptors Containing Dipyridine or Phenanthroline Units: Clues for the Design of Fluorescent Chemosensors for Metal Ions

Diversity-Oriented Synthesis of Morpholine-Containing Molecular Scaffolds

One Hundred Years of the Italian Chemical Society—One Hundred Years of Chemistry

The Birth of a Chemical Society

From Azides to Nitrogen-Centered Radicals: Applications of Azide Radical Chemistry to Organic Synthesis

Stanislao Cannizzaro and the Development of Chemistry in Palermo from 1862 to 1871

Release of Toxic $Gd^{3+}$ Ions to Tumour Cells by $Vitamin B_{12}$ Bioconjugates

A Study of the Influence of Ionic Liquids Properties on the Kemp Elimination Reaction

A Straightforward Total Synthesis of (−)-Chaetominine

Fifty Years of Chemical Research at Farmitalia

The Role of Building-Block Metrics in the Halogen-Bonding-Driven Self-Assembly of Calixarenes, Inorganic Salts and Diiodoperfluoroalkanes

Stereospecific Synthesis of $β^{3}-Amino$ Acid Derivatives from Propargylic Alcohols: Efficient Solution-Phase Synthesis of Oligopeptides without Coupling Agents

Magnetism in Nanoparticles: Beyond the Effect of Particle Size

Is the Backbone Conformation of $C^{α}-Methyl$ Proline Restricted to a Single Region?

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Iron-Substituted Polyoxotungstates as Inorganic Synzymes: Evidence for a Biomimetic Pathway in the Catalytic Oxygenation of Catechols

Electrochemical Characterisation of 6-Iodomaltose, 6′-Iodomaltose and 6-Iodomaltotriose on a Silver Cathode and Their One-Pot Electrochemical Dimerisation to New Mixed O/C Maltotetraose and Maltohexaose Mimics

Regio- and Stereoselectivity in the Decatungstate Photocatalyzed Alkylation of Alkenes by Alkylcyclohexanes

Characterisation of the MMP-12–Elastin Adduct

Oxygen-Atom Transfer by a Naked Manganese(V)–Oxo–Porphyrin Complex Reveals Axial Ligand Effect

On the Dichotomic Reactivity of Lithiated Styrene Oxide: A Computational and Multinuclear Magnetic Resonance Investigation

Year: 2009 Volume: 15 Issue: 31

Year: 2009 Volume: 15 Issue: 30

Year: 2009 Volume: 15 Issue: 29

Year: 2009 Volume: 15 Issue: 28

Year: 2009 Volume: 15 Issue: 27

Year: 2009 Volume: 15 Issue: 26

Year: 2009 Volume: 15 Issue: 25

Year: 2009 Volume: 15 Issue: 24

Year: 2009 Volume: 15 Issue: 23

Year: 2009 Volume: 15 Issue: 22

Year: 2009 Volume: 15 Issue: 21

Year: 2009 Volume: 15 Issue: 20

Year: 2009 Volume: 15 Issue: 19

Year: 2009 Volume: 15 Issue: 18

Year: 2009 Volume: 15 Issue: 17

Year: 2009 Volume: 15 Issue: 16

Year: 2009 Volume: 15 Issue: 15

Year: 2009 Volume: 15 Issue: 14

Year: 2009 Volume: 15 Issue: 13

Year: 2009 Volume: 15 Issue: 12

Year: 2009 Volume: 15 Issue: 11

Year: 2009 Volume: 15 Issue: 10

Year: 2009 Volume: 15 Issue: 9

Year: 2009 Volume: 15 Issue: 8

Year: 2009 Volume: 15 Issue: 7

Year: 2009 Volume: 15 Issue: 6

Year: 2009 Volume: 15 Issue: 5

Year: 2009 Volume: 15 Issue: 4

Year: 2009 Volume: 15 Issue: 3

Year: 2009 Volume: 15 Issue: 2

Year: 2009 Volume: 15 Issue: 1

Year: 2008 Volume: 14

Year: 2007 Volume: 13

Year: 2006 Volume: 12

Year: 2005 Volume: 11

Year: 1997 Volume: 3

Regio- and Stereoselectivity in the Decatungstate Photocatalyzed Alkylation of Alkenes by Alkylcyclohexanes

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Dondi, Daniele Fagnoni, Maurizio Albini, Angelo Mella, Mariella Maldotti, Andrea Ravelli, Davide Molinari, Alessandra
Description	Author Affiliation: Dondi D ( Department of General Chemistry v. Taramelli 12, 27100 Pavia, Italy.)
Abstract	Tetrabutylammonium decatungstate (WO) photocatalyzes radical alkylation reactions starting directly from alkanes. When using tert-butylcyclohexane and methylcyclohexane as the radical precursors, the addition to electrophilic alkenes (β,β-dialkylmethylenemalononitriles, acrylonitrile, methyl acrylate, methyl vinyl ketone) is regioselective and exclusively gives 3- and 4-substituted cyclohexyl adducts, with no significant functionalization of the other positions. Furthermore, when a β,β-disubstituted alkene is used, the reaction is stereoselective (cis stereochemistry for the 1,3-cyclohexane derivatives and trans for the 1,4 isomers). Some of the reactions have also been carried out by using benzophenone as the photocatalyst, giving the same product distribution. However, the decatungstate anion is a superior catalyst from a preparative point of view, because it is efficient at low concentrations (0.002 m, 2 mol %) and allows for a simple work up. From a mechanistic point of view, the role of both the alkyl radicals and the radical adducts has been assessed by trapping experiments in the presence of suitable additives (α-phenyl-N-tert-butylnitrone, PBN, and 2-methyl-2-nitrosopropane, MNP) and by EPR spectroscopic detection of the resulting nitroxides in solution. Furthermore, trapping by the nitroxide TEMPO (TEMPO=2,2,6,6-tetramethylpiperidine N-oxide) gives O-(tert-butylcyclohexyl)hydroxylamines, again as only the 3- and the 4-substituted isomers. We conclude that the observed regioselective activation originates from the initial hydrogen abstraction step (the statistically corrected ratio for positions 3 and 4 ranges from 1.1 to 1.35 for all of the trapping products). The selectivity is mainly due to steric hinderence.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	32
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-08-10
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

Central Library (ISO-9001:2015 Certified)
Indian Institute of Technology Kharagpur
Kharagpur, West Bengal, India | PIN - 721302

See location in the Map
03222 282435
Mail: support@ndl.gov.in

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in