Jean-Pierre Demoute - Academia.edu (original) (raw)
Papers by Jean-Pierre Demoute
THE INVENTION IS INTENDED TO ILLUSTRATE WITH NEW EXAMPLES OF FORMULA (I) OF THE PATENT APPLICATIO... more THE INVENTION IS INTENDED TO ILLUSTRATE WITH NEW EXAMPLES OF FORMULA (I) OF THE PATENT APPLICATION MAIN AND BRING NEW EXAMPLES RELATED TO THE FORMULA (I) AND ANSWERING THE GENERAL FORMULA (I ): (CF DRAWING IN BOPI) wherein R represents OR an alkyl radical, optionally substituted, or a CLUSTER optionally substituted aryl, or a radical HETEROCYCLIC optionally substituted, B is OR A RADICAL I RENT, OR THE rEST OF USED ALCOHOL SYNTHESIS OF ESTERS AND SERIES pyrethroid X REPRESENTS AN ATOM HALOGENE THE DOUBLE BOND WITH ETHYLENE GEOMETRY OR E Z. PRODUCTS OF INVENTION MAY BE USED IN PEST ANIMALS, PESTS OF PLANTS AND PESTS OF LOCAL.
Organic Letters, Jan 26, 2011
The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyc... more The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyclopropyl iodides, allowing an efficient access to a wide variety of functionalized alkynyl cyclopropanes.
![Research paper thumbnail of [3,3]-Sigmatropic Rearrangement of Cyclopropenylcarbinyl Cyanates: Access to Alkylidene(aminocyclopropane) Derivatives](https://attachments.academia-assets.com/114161588/thumbnails/1.jpg)
](Chemistry: A European Journal, Sep 10, 2018
Cyclopropenylcarbinyl cyanates, generated in situ by dehydration of the corresponding carbamates,... more Cyclopropenylcarbinyl cyanates, generated in situ by dehydration of the corresponding carbamates, undergo an efficient and stereoselective [3,3]-sigmatropic rearrangement leading to the corresponding alkylidene(isocyanatocyclopropanes) that can be converted into various alkylidene(aminocyclopropane) derivatives in a one-pot manner. This transformation complements the repertoire of sigmatropic rearrangements involving cyclopropenylcarbinol derivatives and in particular the previously reported Overman rearrangement of cyclopropenylcarbinyl trichloroacetimidates.
Tetrahedron Letters, 1994
Sodium azide (13.8 mmol) was added to a solution of chloropyrimidine (11.52 mmol) in DMF (12 ml).... more Sodium azide (13.8 mmol) was added to a solution of chloropyrimidine (11.52 mmol) in DMF (12 ml). The reaction warmed slightly and NaCl precipitated. After stirring for 10 min at 2025°, the reaction was poured onto 120 ml of water. After filtration of the slight ...
![Research paper thumbnail of A Sonogashira Cross-Coupling/5-<i>exo</i>-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4-Substituted 3-Azabicyclo[3.1.0]hexan-2-ones from 2-Iodocyclopropanecarboxamides](https://attachments.academia-assets.com/114161587/thumbnails/1.jpg)
](Journal of Organic Chemistry, May 15, 2013
Synthesis, 1990
We describe three stereoselective syntheses of deltametrin, one of the most potent industrially a... more We describe three stereoselective syntheses of deltametrin, one of the most potent industrially available insecticides, from γ-alkoxy-α,β-unsaturated carbonyl compounds, isopropyldiphenylsulfonium tetrafluoroborate and potassium tert-butoxide
Pesticide Science, 1989
Pyrethroids are a class of lipophilic insecticide very easily degraded in the natural environment... more Pyrethroids are a class of lipophilic insecticide very easily degraded in the natural environment. The two main routes of degradution, photo-and biodegradation, are ojien superimposed. Pyrethroids developed jor use in agriculture are much more photostable than the natural pyrethrins or early synthetic derivatives but they are still sensitive to sunlight, which triggers many alterations such as isomerisatioti or ester cleavage. The basic puthways of pyrethroid metabolism include hydrolysis of the central ester linkage arid oxidation of both acid and alcohol moieties. The rate of these metubolic transformations and the nature of the metabolites depend mainly on the organism involved, Birds and mammals metabolise and excrete more rapidly than insects and fishes. In plants, initial metabolic processes are identical to those known in animals. In soil, pyrethroids undergo the same type o f trunsformution, hydrolysis and o.xidution. Neither degradation products nor intact purent compounds are leached.
ChemInform, Sep 18, 1990
Halogen compounds P 0030 A Straightforward Synthesis of Alkenyl Nonaflates from Carbonyl Compound... more Halogen compounds P 0030 A Straightforward Synthesis of Alkenyl Nonaflates from Carbonyl Compounds Using Nonafluorobutane-1-sulfonyl Fluoride in Combination with Phosphazene Bases.-A general chemo-and regioselective synthesis of alkenyl nonaflates uses purified fluoride (II) and a phosphazene base. The regioselectivity of the process [e.g. for (VIII)] can be significantly influenced by the type of phosphazene base.-(VOGEL,
Bulletin de la Société Chimique de France, 1996
Organic Letters, Jul 17, 2015
Glycolates or glycinates derived from diversely substituted secondary cyclopropenylcarbinols have... more Glycolates or glycinates derived from diversely substituted secondary cyclopropenylcarbinols have been involved for the first time in an Ireland-Claisen rearrangement. This reaction allows an efficient and stereoselective access to highly functionalized alkylidenecyclopropanes possessing an α-hydroxy or α-amino acid subunit, which in turn are valuable precursors of substituted cyclopropanes by diastereoselective hydrogenation of the exocyclic alkene.
European Journal of Organic Chemistry, Jan 19, 2015
The diastereoselectivity of the Pictet-Spengler cyclization of bicyclic N-acyliminium ions that c... more The diastereoselectivity of the Pictet-Spengler cyclization of bicyclic N-acyliminium ions that contain a 3-azabicyclo-[n.3.0]alkane core and an electron-rich π-nucleophilic moiety, such as an indol-2-yl, indol-3-yl, 1-methylpyrrol-2-yl, or 3,5-dimethoxyphenyl group, was examined. The N-acyliminium ions were generated by protonation of the corresponding enamides or hemiaminals, which were derived
Tetrahedron Letters, Jun 1, 1997
... Chem. Soc. 1994, 116, 69856986. (d) Wright, SW; Hageman, DL; McClure, LDJ Org. Chem. 1994, 59... more ... Chem. Soc. 1994, 116, 69856986. (d) Wright, SW; Hageman, DL; McClure, LDJ Org. Chem. 1994, 59, 60956097. ... 6985–6986. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (135). 3. (d). SW Wright, DL Hageman and LD McClure. J. Org. Chem. ...
ChemInform, May 12, 2011
Copper-Free Sonogashira Coupling in Water with Linear Polystyrene-Stabilized PdO Nanoparticles.-T... more Copper-Free Sonogashira Coupling in Water with Linear Polystyrene-Stabilized PdO Nanoparticles.-The method is investigated with various aryl iodides and bromobenzene. The catalyst can be easily recovered and reused at least 4 times without loss of activity.-(TERATANI, T.
ChemInform, Aug 19, 2010
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform, Jan 27, 2004
For Abstract see ChemInform Abstract in Full Text.
![Research paper thumbnail of ChemInform Abstract: A Sonogashira Cross-Coupling/5-exo-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4-Substituted 3-Azabicyclo[3.1.0]hexan-2-ones from 2-Iodocyclopropanecarboxamides](https://attachments.academia-assets.com/114161577/thumbnails/1.jpg)
](ChemInform, Sep 19, 2013
Sonogashira Cross-Coupling of Arenediazonium Salts.-The title compounds are alkynylated by a domi... more Sonogashira Cross-Coupling of Arenediazonium Salts.-The title compounds are alkynylated by a domino iododediazoniation/Sonogashira cross-coupling using various terminal alkynes and a variety of functionalities is tolerated for both types of substrates. Synthesis of the arenediazonium salts and the iododediazoniation/Sonogashira cross-coupling sequence can also be performed as a one-pot process [cf. (IIId,e)]. 2-Phenylindole (X) is successfully prepared by subsequent treatment of (IX) with NaAuCl4.-(FABRIZI, G.
Synthesis, Feb 1, 1995
ABSTRACT
THE INVENTION IS INTENDED TO ILLUSTRATE WITH NEW EXAMPLES OF FORMULA (I) OF THE PATENT APPLICATIO... more THE INVENTION IS INTENDED TO ILLUSTRATE WITH NEW EXAMPLES OF FORMULA (I) OF THE PATENT APPLICATION MAIN AND BRING NEW EXAMPLES RELATED TO THE FORMULA (I) AND ANSWERING THE GENERAL FORMULA (I ): (CF DRAWING IN BOPI) wherein R represents OR an alkyl radical, optionally substituted, or a CLUSTER optionally substituted aryl, or a radical HETEROCYCLIC optionally substituted, B is OR A RADICAL I RENT, OR THE rEST OF USED ALCOHOL SYNTHESIS OF ESTERS AND SERIES pyrethroid X REPRESENTS AN ATOM HALOGENE THE DOUBLE BOND WITH ETHYLENE GEOMETRY OR E Z. PRODUCTS OF INVENTION MAY BE USED IN PEST ANIMALS, PESTS OF PLANTS AND PESTS OF LOCAL.
Organic Letters, Jan 26, 2011
The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyc... more The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyclopropyl iodides, allowing an efficient access to a wide variety of functionalized alkynyl cyclopropanes.
Chemistry: A European Journal, Sep 10, 2018
Cyclopropenylcarbinyl cyanates, generated in situ by dehydration of the corresponding carbamates,... more Cyclopropenylcarbinyl cyanates, generated in situ by dehydration of the corresponding carbamates, undergo an efficient and stereoselective [3,3]-sigmatropic rearrangement leading to the corresponding alkylidene(isocyanatocyclopropanes) that can be converted into various alkylidene(aminocyclopropane) derivatives in a one-pot manner. This transformation complements the repertoire of sigmatropic rearrangements involving cyclopropenylcarbinol derivatives and in particular the previously reported Overman rearrangement of cyclopropenylcarbinyl trichloroacetimidates.
Tetrahedron Letters, 1994
Sodium azide (13.8 mmol) was added to a solution of chloropyrimidine (11.52 mmol) in DMF (12 ml).... more Sodium azide (13.8 mmol) was added to a solution of chloropyrimidine (11.52 mmol) in DMF (12 ml). The reaction warmed slightly and NaCl precipitated. After stirring for 10 min at 2025°, the reaction was poured onto 120 ml of water. After filtration of the slight ...
Journal of Organic Chemistry, May 15, 2013
Synthesis, 1990
We describe three stereoselective syntheses of deltametrin, one of the most potent industrially a... more We describe three stereoselective syntheses of deltametrin, one of the most potent industrially available insecticides, from γ-alkoxy-α,β-unsaturated carbonyl compounds, isopropyldiphenylsulfonium tetrafluoroborate and potassium tert-butoxide
Pesticide Science, 1989
Pyrethroids are a class of lipophilic insecticide very easily degraded in the natural environment... more Pyrethroids are a class of lipophilic insecticide very easily degraded in the natural environment. The two main routes of degradution, photo-and biodegradation, are ojien superimposed. Pyrethroids developed jor use in agriculture are much more photostable than the natural pyrethrins or early synthetic derivatives but they are still sensitive to sunlight, which triggers many alterations such as isomerisatioti or ester cleavage. The basic puthways of pyrethroid metabolism include hydrolysis of the central ester linkage arid oxidation of both acid and alcohol moieties. The rate of these metubolic transformations and the nature of the metabolites depend mainly on the organism involved, Birds and mammals metabolise and excrete more rapidly than insects and fishes. In plants, initial metabolic processes are identical to those known in animals. In soil, pyrethroids undergo the same type o f trunsformution, hydrolysis and o.xidution. Neither degradation products nor intact purent compounds are leached.
ChemInform, Sep 18, 1990
Halogen compounds P 0030 A Straightforward Synthesis of Alkenyl Nonaflates from Carbonyl Compound... more Halogen compounds P 0030 A Straightforward Synthesis of Alkenyl Nonaflates from Carbonyl Compounds Using Nonafluorobutane-1-sulfonyl Fluoride in Combination with Phosphazene Bases.-A general chemo-and regioselective synthesis of alkenyl nonaflates uses purified fluoride (II) and a phosphazene base. The regioselectivity of the process [e.g. for (VIII)] can be significantly influenced by the type of phosphazene base.-(VOGEL,
Bulletin de la Société Chimique de France, 1996
Organic Letters, Jul 17, 2015
Glycolates or glycinates derived from diversely substituted secondary cyclopropenylcarbinols have... more Glycolates or glycinates derived from diversely substituted secondary cyclopropenylcarbinols have been involved for the first time in an Ireland-Claisen rearrangement. This reaction allows an efficient and stereoselective access to highly functionalized alkylidenecyclopropanes possessing an α-hydroxy or α-amino acid subunit, which in turn are valuable precursors of substituted cyclopropanes by diastereoselective hydrogenation of the exocyclic alkene.
European Journal of Organic Chemistry, Jan 19, 2015
The diastereoselectivity of the Pictet-Spengler cyclization of bicyclic N-acyliminium ions that c... more The diastereoselectivity of the Pictet-Spengler cyclization of bicyclic N-acyliminium ions that contain a 3-azabicyclo-[n.3.0]alkane core and an electron-rich π-nucleophilic moiety, such as an indol-2-yl, indol-3-yl, 1-methylpyrrol-2-yl, or 3,5-dimethoxyphenyl group, was examined. The N-acyliminium ions were generated by protonation of the corresponding enamides or hemiaminals, which were derived
Tetrahedron Letters, Jun 1, 1997
... Chem. Soc. 1994, 116, 69856986. (d) Wright, SW; Hageman, DL; McClure, LDJ Org. Chem. 1994, 59... more ... Chem. Soc. 1994, 116, 69856986. (d) Wright, SW; Hageman, DL; McClure, LDJ Org. Chem. 1994, 59, 60956097. ... 6985–6986. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (135). 3. (d). SW Wright, DL Hageman and LD McClure. J. Org. Chem. ...
ChemInform, May 12, 2011
Copper-Free Sonogashira Coupling in Water with Linear Polystyrene-Stabilized PdO Nanoparticles.-T... more Copper-Free Sonogashira Coupling in Water with Linear Polystyrene-Stabilized PdO Nanoparticles.-The method is investigated with various aryl iodides and bromobenzene. The catalyst can be easily recovered and reused at least 4 times without loss of activity.-(TERATANI, T.
ChemInform, Aug 19, 2010
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform, Jan 27, 2004
For Abstract see ChemInform Abstract in Full Text.
ChemInform, Sep 19, 2013
Sonogashira Cross-Coupling of Arenediazonium Salts.-The title compounds are alkynylated by a domi... more Sonogashira Cross-Coupling of Arenediazonium Salts.-The title compounds are alkynylated by a domino iododediazoniation/Sonogashira cross-coupling using various terminal alkynes and a variety of functionalities is tolerated for both types of substrates. Synthesis of the arenediazonium salts and the iododediazoniation/Sonogashira cross-coupling sequence can also be performed as a one-pot process [cf. (IIId,e)]. 2-Phenylindole (X) is successfully prepared by subsequent treatment of (IX) with NaAuCl4.-(FABRIZI, G.
Synthesis, Feb 1, 1995
ABSTRACT