GB1207372A - Aryl sulphones - Google Patents

Aryl sulphones

Info

Publication number
GB1207372A
GB1207372A GB836770A GB836770A GB1207372A GB 1207372 A GB1207372 A GB 1207372A GB 836770 A GB836770 A GB 836770A GB 836770 A GB836770 A GB 836770A GB 1207372 A GB1207372 A GB 1207372A
Authority
GB
United Kingdom
Prior art keywords
methyl
unsaturated
ethyl
radical
saturated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB836770A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1207372A publication Critical patent/GB1207372A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/14Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing bromine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C22/00Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
    • C07C22/02Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
    • C07C22/04Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/04Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
    • C07C35/045Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings containing a four-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41Preparation of salts of carboxylic acids
    • C07C51/412Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • C07C51/487Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58Preparation of carboxylic acid halides
    • C07C51/60Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16Unsaturated compounds
    • C07C61/35Unsaturated compounds having unsaturation outside the rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16Unsaturated compounds
    • C07C61/40Unsaturated compounds containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/42Singly bound oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12CBEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00Fermentation processes for beer
    • C12C11/02Pitching yeast

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,207,372. Aryl sulphones. ROUSSEL UCLAF. 29 Aug., 1967 [26 Aug., 1966(2); 24 Feb., 1967; 16 June, 1967; 19 July, 1967], No. 8367/70. Divided out of 1,207,371. Heading C2C. The invention comprises aryl sulphones of the general formula: H-A-SO 2 -Ar wherein Ar is an aryl group having either one or two aromatic rings which may be substituted with one or more C 1 -C 2 alkyl, alkoxy, halogenomethyl and/or nitro groups or halogen atoms and A is either the radical: or the radical: or the radical in which R 1 is a hydrogen atom or a lower C 1 -C 4 alkyl radical, R 2 and R 3 which may be the same or different are each alkyl, aralkyl, aryl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or heterocyclic radical, R 3 having at least 2 carbon atoms, or R 2 and R 3 together with the intervening carbon atom form a saturated carbocyclic ring with 3 to 7 carbon atoms or an unsaturated carbocyclic ring, e.g. a cyclohexene or cyclopentadiene ring, such carbocyclic rings if desired being substituted by one or more methyl, ethyl and/or methoxy or ethoxy groups, or R 2 and R 3 together with the intervening carbon atom form a polynuclear aromatic system such as fluorene, or a heterocycle which may be substituted by one or more methyl, ethyl and/or methoxy or ethoxy groups, R 4 is a methyl or ethyl group, R 5 is a hydrogen atom or methyl or ethyl group, or R 4 and R 5 form together with the two intervening carbon atoms a saturated or unsaturated heterocyclic or carbocyclic ring, Y is -CH 2 - or a saturated or unsaturated aliphatic hydrocarbon chain and Y<SP>1</SP> is a methine group or a saturated or unsaturated aliphatic hydrocarbon chain. They may be obtained by reacting ArSO 2 M wherein M is an alkali metal, e.g. Na or K, with an allylic type derivative HAX wherein X is Cl, Br or I or a methane sulphonyloxy or toluene-psulphonyloxy group, advantageously in the presence of a solvent and in the presence of a basic reagent. In a modification the products are obtained by reacting the compounds ArSO 2 M with an alcohol HA-OH in the presence of formic acid. 3 - Ethyl - 1 - penten - 3 - ol is obtained from the reaction of pentan-3-one with vinyl magnesium chloride in tetrahydrofuran and then treating with water and is converted into 1 - bromo - 3 - ethyl - 2 - pentene by reaction with PBr 3 in petroleum ether. Several other analogous unsaturated alcohols and unsaturated bromo compounds of the type HABr are also specified and are obtained similarly starting with the appropriate unsaturated ketone. 3 - Methyl - 2 - cyclohexen - 1 - ol is obtained by the action of lithium aluminium hydride on 3-methyl-2-cyclohexen- 1-one in tetrahydrofuran.
GB836770A 1966-08-26 1967-08-29 Aryl sulphones Expired GB1207372A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR74405A FR1505423A (en) 1966-08-26 1966-08-26 New derivatives of cyclopropane and method of preparation
FR74404A FR1507192A (en) 1966-08-26 1966-08-26 Novel aryl allylsulfones and method of preparation
FR96425A FR1527844A (en) 1966-08-26 1967-02-24 New acids and esters derived from cyclopropane and method of preparation
FR110719A FR93112E (en) 1966-08-26 1967-06-16 New derivatives of cyclopropane and method of preparation.
FR114833A FR94309E (en) 1966-08-26 1967-07-19 New cyclopropane derivatives and method of preparation.

Publications (1)

Publication Number Publication Date
GB1207372A true GB1207372A (en) 1970-09-30

Family

ID=38863090

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3954267A Expired GB1207371A (en) 1966-08-26 1967-08-29 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties
GB836770A Expired GB1207372A (en) 1966-08-26 1967-08-29 Aryl sulphones

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3954267A Expired GB1207371A (en) 1966-08-26 1967-08-29 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties

Country Status (14)

Country Link
AT (2) AT289754B (en)
BE (1) BE702662A (en)
CH (3) CH509961A (en)
CS (3) CS180551B2 (en)
DE (1) DE1668603B2 (en)
DK (3) DK140720B (en)
ES (3) ES344435A1 (en)
FR (5) FR1505423A (en)
GB (2) GB1207371A (en)
IL (2) IL38182A (en)
NL (2) NL162060C (en)
SE (2) SE391330B (en)
SU (1) SU691076A3 (en)
YU (5) YU33952B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3714153A (en) * 1970-06-22 1973-01-30 Roussel Uclaf Novel cyclopropanecarboxylic acids
US4045469A (en) 1971-06-25 1977-08-30 The Procter & Gamble Company Insecticidal esters of spiro carboxylic acids
BE791304A (en) * 1971-11-12 1973-05-14 Procter & Gamble 1-ACENAPHTENOL ESTERS
DE2326077C2 (en) * 1972-05-25 1985-12-12 National Research Development Corp., London Unsaturated cyclopropanecarboxylic acids and their derivatives, their preparation and insecticides containing them
HU168432B (en) * 1973-08-15 1976-04-28
DE2857020A1 (en) * 1977-07-04 1981-01-08 Astra Laekemedel Ab A NOVEL INTERMEDIATE FOR PREPARATION OF THERAPEUTICALLY ACTIVE PYRIDINE COMPOUNDS
DE2730515A1 (en) * 1977-07-06 1979-01-18 Bayer Ag SUBSTITUTED PHENOXYBENZYLOXYCARBONYL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES
FR2426673A1 (en) * 1978-05-25 1979-12-21 Nat Res Dev PYRETHRINE TYPE PESTICIDES
FR2428029A1 (en) * 1978-06-06 1980-01-04 Roussel Uclaf ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS SUBSTITUTED BY A-CYANE ALCOHOL, PROCESS FOR THEIR PREPARATION AND INSECTICIDE OR NEMATICIDE COMPOSITIONS CONTAINING THEM
FR2443452A1 (en) * 1978-12-08 1980-07-04 Roussel Uclaf NEW PROCESS FOR THE SPLITTING OF DL CIS ACID AND DL CHRYSANTHEMIC TRANS
FR2455024A1 (en) * 1979-04-03 1980-11-21 Roussel Uclaf NEW PROCESS FOR THE SPLITTING OF ACIDS D, L-CIS 2,2-DIMETHYL 3- (2 ', 2'-DIHALOVINYL) CYCLOPROPANE-1-CARBOXYLIC
FR2455018A1 (en) * 1979-04-26 1980-11-21 Roussel Uclaf ALLETHROLONE DERIVATIVES AND THEIR PREPARATION PROCESS
DE2926671A1 (en) * 1979-07-02 1981-01-15 Bayer Ag METHOD FOR THE PRODUCTION OF CYCLOPROPANE-CARBONIC ACID DERIVATIVES AND NEW INTERMEDIATE PRODUCTS THEREFOR AND METHOD FOR THE PRODUCTION THEREOF
FR2479192A1 (en) * 1980-03-28 1981-10-02 Roussel Uclaf PROCESS FOR THE PREPARATION OF TETRA-SUBSTITUTED CYCLOPROPANIC DERIVATIVES
FR2490633A1 (en) 1980-09-24 1982-03-26 Roussel Uclaf PROCESS FOR THE PREPARATION OF CYCLOPROPANE CARBOXYLIC ACID DERIVATIVES WITH ALDEHYDE FUNCTION
US5504245A (en) * 1994-09-30 1996-04-02 Eastman Chemical Company Processes for the preparation of cyclopropanecarboxylic acid and derivatives thereof

Also Published As

Publication number Publication date
CS180598B2 (en) 1978-01-31
SE369517B (en) 1974-09-02
NL162060B (en) 1979-11-15
NL172853B (en) 1983-06-01
FR93112E (en) 1969-02-14
DK140720C (en) 1980-04-21
FR1527844A (en) 1968-06-07
DK131538B (en) 1975-08-04
NL6711770A (en) 1968-02-27
DE1793721B2 (en) 1976-12-23
YU33952B (en) 1978-09-08
ES350839A1 (en) 1969-05-16
FR1507192A (en) 1967-12-29
DK140720B (en) 1979-11-05
SE391330B (en) 1977-02-14
DE1668603C3 (en) 1974-08-22
YU290379A (en) 1983-10-31
NL172853C (en) 1983-11-01
YU35568B (en) 1981-04-30
GB1207371A (en) 1970-09-30
CH491071A (en) 1970-05-31
DE1668603B2 (en) 1974-01-17
DE1668603A1 (en) 1971-07-01
SU691076A3 (en) 1979-10-05
FR94309E (en) 1969-08-01
ES344435A1 (en) 1968-10-16
AT287671B (en) 1971-02-10
NL162060C (en) 1980-04-15
CH491851A (en) 1970-06-15
NL7906529A (en) 1980-01-31
BE702662A (en) 1968-02-14
YU168567A (en) 1980-10-31
DK131538C (en) 1976-01-05
CS180551B2 (en) 1978-01-31
DK133579C (en) 1976-11-01
DK133579B (en) 1976-06-14
YU33942B (en) 1978-09-08
DE1793721A1 (en) 1972-10-19
AT289754B (en) 1971-03-15
CS180599B2 (en) 1978-01-31
IL38182A (en) 1975-11-25
CH509961A (en) 1971-07-15
ES344436A1 (en) 1968-10-16
IL28541A (en) 1975-11-25
YU168467A (en) 1978-02-28
YU42168A (en) 1978-02-28
FR1505423A (en) 1967-12-15

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PS Patent sealed
PE20 Patent expired after termination of 20 years