Abstract: A novel process for the preparation of sulfonic acid esters containing a lactonic ring comprising compounds in the trans form in the 4- and 5-positions having (4SR,5RS), (4S,5R) or (4R,5S) configuration of the formula ##STR1## wherein Z is selected from the group consisting of alkyl of 1 to 4 carbon atoms and cycloalkyl and monocyclic aryl optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and nitro and R is organic residue of an optionally chiral alcohol of the formula ROH and a process using the compounds of formula I to prepare compounds of (1RS, 4RS, 5SR), (1S, 4S, 5R) or (1R, 4R, 5S) configuration of the formula ##STR2## wherein X is selected from the group consisting of hydrogen and R useful for the preparation of insecticidally active esters.
Type:
Grant
Filed:
July 27, 1983
Date of Patent:
November 19, 1985
Assignee:
Roussel Uclaf
Inventors:
Jacques Martel, Jean Tessier, Jean-Pierre Demoute
Abstract: A process for the preparation of racemic or optically active isomers of alkyl esters of cis chrysanthemic of the formula ##STR1## wherein R is alkyl of 1 to 6 carbon atoms comprising reacting a racemic or optically active cis compound of the formula ##STR2## wherein R has the above definition with an aryl halothioformate of the formula ##STR3## wherein Hal is a halogen and Ar is aryl of 6 to 12 carbon atoms optionally substituted with at least one alkyl of 1 to 3 carbon atoms to obtain a compound of the formula ##STR4## of cis configuration and heating the latter optionally in an organic solvent to obtain the compound of formula I and novel intermediates.
Type:
Grant
Filed:
July 18, 1984
Date of Patent:
November 5, 1985
Assignee:
Roussel Uclaf
Inventors:
Michel Frank-Neumann, Madjid Sedrati, Jean-Pierre Vigneron, Vincente Bloy
Abstract: Novel ethers of organic compounds containing chiral atoms of the formula ##STR1## wherein A is a hydrocarbonated chain of 1 to 10 groups, the said chain containing one or more heteroatoms, one or more unsaturations, the assembly of the groups constituting the chain may represent a mono- or polycyclic system, including a system of the spiro or endo type, the chain A can contain one or more chiral atoms or the lactone moiety can present a chirality due to the dissymmetric spatial configuration of the whole of the molecule and Z is selected from the group consisting of primary, secondary or tertiary alcohol moiety containing at least an asymmetric carbon atom, a phenol moiety substituted comprising at least one asymmetric carbon atom and a substituted alcohol or phenol moiety with a chirality due to the dissymmetric spatial configuration of the whole of the molecule, with the proviso Z is not (R) or (S) .alpha.
Type:
Grant
Filed:
December 6, 1982
Date of Patent:
September 10, 1985
Assignee:
Roussel Uclaf
Inventors:
Jacques Martel, Jean Tessier, Andre Teche
Abstract: Lactones of the formula ##STR1## wherein R is hydrogen or a CX.sub.3 group, and each X is a chlorine or bromine atom, are converted to the known cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acids or lower alkyl esters, from which pyrethroid insecticides are obtained.
Abstract: A lactone of the formula: ##STR1## wherein R.sub.1 through R.sub.8 are independently hydrogen or C.sub.1-5 alkyl, obtained by decarboxylation condensation reaction of a saturated alicyclic 1,2-dicarboxylic acid anhydride, is a good curing agent for thermosetting resins.
Abstract: A novel alkyl 4-methyl-3-formyl-penten-1-oate of the formula ##STR1## wherein R is alkyl of 1 to 5 carbon atoms and the dotted lines represent a double bond in the 3,4 or 4,5-position and their preparation and novel intermediates therefore and a novel process for the preparation of 4-methyl-3-formyl-pent-3-en-1-oic acid which is an intermediate for the preparation of compounds of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of hydrogen and the residue of an alcohol R.sub.3 OH by the process of European Patent Application Ser. No. 0023849 published Feb. 11, 1981, which are used to prepare very active insecticidal esters.
Type:
Grant
Filed:
April 21, 1983
Date of Patent:
December 11, 1984
Assignee:
Roussel Uclaf
Inventors:
Jacques Martel, Jean Tessier, Jean-Pierre Demoute
Abstract: Process for selective homogeneous catalytic hydrogenation of carboxylic acid anhydrides to ester or lactones at an improved rate and to obtain improved yields wherein the catalyst is a ruthenium trichlorostannate complex of the formula: ##STR1## wherein X is hydrogen, chlorine, bromine, iodine or lower alkyl; m is the integer 1 or 2; n is an integer of from 0 to 3 but when n is 2 or 3, X may be the same or different; M is P, As or Sb; R.sup.6, R.sup.7 and R.sup.8 independently are lower alkyl, cycloalkyl, aryl, benzyl or a bidentate legand; x is an integer of from 1 to 4 but when x is 2 or more, M may be the same or different; L is a neutral ligand, olefin, CO or (R.sup.9).sub.2 CO wherein R.sup.9 is lower alkyl; y is an integer of from 0 to 3 but when y is 2 or 3, L may be the same or different; and the sum of x and y is at least 2.
Abstract: The rate of selective hydrogenation of carboxylic acid anhydrides to esters or lactones in the presence of a ruthenium organophosphorous catalyst which contains or liberates a hydrogen halide during the hydrogenation, is improved by providing in the reaction medium prior to or during the hydrogenation a basic amino compound to remove the hydrogen halide.
Abstract: Novel 3-formyl-4-methyl-pent-3-ene-1-oic acid of the formula ##STR1## and a process for its preparation and intermediates and a process for the preparation of compounds of the formula ##STR2## wherein W is selected from the group consisting of hydrogen and R.sub.1 of an optionally chiral alcohol R.sub.1 OH, useful as an intermediate for the producton of numerous ester having elevated insecticidal activity.
Type:
Grant
Filed:
July 1, 1982
Date of Patent:
April 17, 1984
Assignee:
Roussel Uclaf
Inventors:
Jacques Martel, Jean Tessier, Jean-Pierre Demoute
Abstract: Process for manufacturing chlorolactones by reacting, within an ahydrous organic solvent, a metal N-chlorosulfonamidate of the formula ##STR1## wherein R is a hydrogen or halogen atom or an alkyl radical, Ar is a mono- or polycyclic divalent aromatic radical and M is an alkali metal, with a substantially stoichiometrical proportion of an aliphatic or alicyclic carboxylic acid having at least one double bond separated from the COOH group by at least 2 carbon atoms, in the presence of a substantially stoichiometrical amount of a strong acid whose conjugate base is weakly nucleophilic.
Type:
Grant
Filed:
November 13, 1981
Date of Patent:
November 1, 1983
Assignee:
Institut Francais du Petrole
Inventors:
Bernard Damin, Alain Forestiere, Bernard Sillion
Abstract: Di- and tetrahydrobenzofuranone of the formula ##STR1## are useful in scenting and/or flavoring agents for imparting thereto a coumarin and coconut note.
Abstract: Novel compounds of the formula I ##STR1## in which each of Y.sup.1 and Y.sup.2 independently represents a fluorine, chlorine or bromine atom and each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or an alkyl group having up to 10 carbon atoms, or R.sup.1 and R.sup.2 together represent an alkylene group having from 2 to 5 carbon atoms, may be converted by the action of base into the corresponding dihalovinylcyclopropane carboxylic acids.
Abstract: Novel ethers of organic compounds containing chiral atoms of the formula ##STR1## wherein A is a hydrocarbonated chain of 1 to 10 groups, the said chain containing one or more heteroatoms, one or more unsaturations, the assembly of the groups constituting the chain may represent a mono- or polycyclic system, including a system of the spiro or endo type, the chain A can contain one or more chiral atoms or the lactone moiety can present a chirality due to the dissymetric spatial configuration of the whole of the molecule and Z is selected from the group consisting of primary, secondary or tertiary alcohol moiety containing at least an asymetric carbon atom, a phenol moiety substituted comprising at least one asymetric carbon atom and an substituted alcohol or phenol moiety with a chirality due to the dissymetric spatial configuration of the whole of the molecule, with the proviso Z is not (R) or (S) .alpha.
Type:
Grant
Filed:
February 6, 1981
Date of Patent:
February 15, 1983
Assignee:
Roussel Uclaf
Inventors:
Jacques Martel, Jean Tessier, Andre Teche
Abstract: Novel compounds of the formula I ##STR1## in which each of Y.sup.1 and Y.sup.2 independently represents a fluorine, chlorine or bromine atom and each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or an alkyl group having up to 10 carbon atoms, or R.sup.1 and R.sup.2 together represent an alkylene group having from 2 to 5 carbon atoms, may be converted by the action of base into the corresponding dihalovinylcyclopropane carboxylic acids which are intermediates for preparing known pyrethroid insecticides.
Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified. The halomethyl bicyclic lactone is a useful intermediate for the preparation of insecticidal cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates or cis-3-(2-halo-2-trihalomethylethenyl)-2,2-dimethylcyclopropanecarboxylates .
Type:
Grant
Filed:
June 23, 1980
Date of Patent:
August 3, 1982
Assignee:
FMC Corporation
Inventors:
Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
Abstract: The novel dihalomethylenelactone of formula (I) can be prepared by the trihalomethylation of an anhydride of formula (II). Reaction of compound (II), wherein R.sub.1 =R.sub.2 =methyl, with CBr.sub.3 COONa in DMF gave at -25.degree. C. the dibromovinyllactone and with CCL.sub.3 COONa in DMF at 0.degree. C. the dichlorovinyllactone. ##STR1## X.sub.1, X.sub.2 and X.sub.3 are halogen atoms and R.sub.1 and/or R.sub.2 are hydrogen atoms and/or alkyl groups with 1-10 carbon atoms;M is alkali, e.g. Na or K. The novel dihalomethylenelactones can also be prepared by treating a compound of formula (III) ##STR2## with phosphorus halide and zinc in an inert, polar aprotic solvent. The compounds are pyrethroid intermediates.
Abstract: Novel sulfonic acid esters containing a lactonic ring comprising compounds in the trans form in the 4- and 5-positions having (4SR, 5RS), (4S, 5R) or (4R, 5S) configuration of the formula ##STR1## wherein Z is selected from the group consisting of alkyl of 1 to 4 carbon atoms and monocyclic aryl optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and nitro and R is organic residue of an optionally chiral alcohol of the formula ROH and a process for their preparation and a process using the compounds of formula I to prepare compounds of (1RS, 4RS, 5SR), (1S, 4S, 5R) or (1R, 4R, 5S) configuration of the formula ##STR2## wherein X is selected from the group consisting of hydrogen and R. The compounds of V are useful for the preparation of cyclopropane carboxylic acids whose esters are known to be very active insecticides.
Type:
Grant
Filed:
July 29, 1980
Date of Patent:
May 25, 1982
Assignee:
Roussel Uclaf
Inventors:
Jacques Martel, Jean Tessier, Jean-Pierre Demoute