FR2320929A1 - Prepn. of 2-(2,2-dihalo vinyl) 3,3-dimethyl cyclopropane derivs. - useful as insecticide intermediates from 2,2-dimethyl 3-butene derivs. - Google Patents

Prepn. of 2-(2,2-dihalo vinyl) 3,3-dimethyl cyclopropane derivs. - useful as insecticide intermediates from 2,2-dimethyl 3-butene derivs.

Info

Publication number
FR2320929A1
FR2320929A1 FR7614733A FR7614733A FR2320929A1 FR 2320929 A1 FR2320929 A1 FR 2320929A1 FR 7614733 A FR7614733 A FR 7614733A FR 7614733 A FR7614733 A FR 7614733A FR 2320929 A1 FR2320929 A1 FR 2320929A1
Authority
FR
France
Prior art keywords
derivs
dimethyl
prepn
butene
useful
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.)
Withdrawn
Application number
FR7614733A
Other languages
French (fr)
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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
Priority claimed from GB20887/75A external-priority patent/GB1519051A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of FR2320929A1 publication Critical patent/FR2320929A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-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
    • C07D307/30—Heterocyclic compounds containing five-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 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

2-(2,2-Dihalovinyl)-3,3-dimethylcyclopropane derivs. of formula (I) are prepd. by reacting a 2,2-dimethyl-but-3-ene deriv. of formula (II) with a tetrahalomethane of formula (III) in the presence of a radical catalyst, and treating the product (IV) with 2 molar equivs. of base. In the formulae X is acetyl, COOH or CN; Z, Q and R are Cl or Br, provided that Q must be Br when either Z or R is Br; Y is acetyl, COOH, CN or 2-5C alkoxycarbonyl. (I; Z=CL, Y = COOH) is an intermediate for the prepn. of insecticides (e.g. its 3-phenoxybenzyl ester). The process avoids the use of explosive and carcinogenic ethyl diazoacetate.
FR7614733A 1975-05-16 1976-05-14 Prepn. of 2-(2,2-dihalo vinyl) 3,3-dimethyl cyclopropane derivs. - useful as insecticide intermediates from 2,2-dimethyl 3-butene derivs. Withdrawn FR2320929A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB2088975 1975-05-16
GB20887/75A GB1519051A (en) 1975-05-16 1975-05-16 Cyclopropane derivatives and their prparation
GB559976 1976-02-12

Publications (1)

Publication Number Publication Date
FR2320929A1 true FR2320929A1 (en) 1977-03-11

Family

ID=27254669

Family Applications (3)

Application Number Title Priority Date Filing Date
FR7614733A Withdrawn FR2320929A1 (en) 1975-05-16 1976-05-14 Prepn. of 2-(2,2-dihalo vinyl) 3,3-dimethyl cyclopropane derivs. - useful as insecticide intermediates from 2,2-dimethyl 3-butene derivs.
FR7700509A Withdrawn FR2351934A1 (en) 1975-05-16 1977-01-10 PROCESS FOR PREPARATION OF CYCLOPROPANE DERIVATIVES AND PRODUCTS OBTAINED
FR7700508A Withdrawn FR2351940A1 (en) 1975-05-16 1977-01-10 HALOGEN HYDROCARBON WITH ACETYL, CARBOXYL OR CYANO FUNCTION

Family Applications After (2)

Application Number Title Priority Date Filing Date
FR7700509A Withdrawn FR2351934A1 (en) 1975-05-16 1977-01-10 PROCESS FOR PREPARATION OF CYCLOPROPANE DERIVATIVES AND PRODUCTS OBTAINED
FR7700508A Withdrawn FR2351940A1 (en) 1975-05-16 1977-01-10 HALOGEN HYDROCARBON WITH ACETYL, CARBOXYL OR CYANO FUNCTION

Country Status (5)

Country Link
JP (1) JPS51141842A (en)
AU (1) AU511487B2 (en)
DE (1) DE2621831A1 (en)
FR (3) FR2320929A1 (en)
NL (1) NL7605172A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2317298A1 (en) * 1975-07-11 1977-02-04 Ici Ltd NEW LACTONS AND THEIR PREPARATION PROCESS
FR2329651A1 (en) * 1975-07-24 1977-05-27 Nat Res Dev PROCESS FOR PREPARATION OF CYCLOPROPANE-CARBOXYLIC ACIDS

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1561502A (en) * 1975-07-22 1980-02-20 Kuraray Co Y-lactone derivatives
GB1503857A (en) * 1976-05-25 1978-03-15 Cheminova As Production of chrysanthemic acid esters and homologues thereof
NZ185635A (en) * 1976-11-18 1980-04-28 Ici Ltd Preparation of 3-dihalovinyl-2,2-dimethylcyclopropane carboxylic acid derivatives
DE2710174A1 (en) * 1977-03-09 1978-09-14 Bayer Ag PROCESS FOR THE MANUFACTURING OF DIHALOGENVINYL CYCLOPROPANIC CARBONIC ACIDS AND THEIR ESTERS
DE2923777A1 (en) * 1979-06-12 1980-12-18 Bayer Ag PROCESS FOR THE MANUFACTURE OF 2-CYANO-3,3-DIMETHYL-CYCLOPROPANE-1-CARBONIC ACID ESTERS AND INTERMEDIATE PRODUCTS FOR ITS PERFORMANCE
DE2937763A1 (en) * 1979-09-19 1981-04-09 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING 5- (2,2-DIHALOGENVINYL) -4,4-DIALKYLTETRAHYDROFURAN-2-ONES

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5195010A (en) * 1975-02-12 1976-08-20 Arukiru 3*5*5*55 tetoraharogenopenchiruketonjudotainoseizohoho
NZ180822A (en) * 1975-05-16 1979-03-16 Ici Ltd Preparation of 2-(2,2-dihalovinyl)-3,3-dimethylcyolopropane carboxylates intermediates
GB1553818A (en) * 1975-07-24 1979-10-10 Nat Res Dev Synthesis of cyclopropane carboxylic acids

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2317298A1 (en) * 1975-07-11 1977-02-04 Ici Ltd NEW LACTONS AND THEIR PREPARATION PROCESS
FR2329651A1 (en) * 1975-07-24 1977-05-27 Nat Res Dev PROCESS FOR PREPARATION OF CYCLOPROPANE-CARBOXYLIC ACIDS

Also Published As

Publication number Publication date
JPS51141842A (en) 1976-12-07
AU1379776A (en) 1977-11-17
FR2351934A1 (en) 1977-12-16
NL7605172A (en) 1976-11-18
AU511487B2 (en) 1980-08-21
FR2351940A1 (en) 1977-12-16
DE2621831A1 (en) 1976-12-02

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