GB1394864A - Unsaturated ethers and thioethers - Google Patents

Unsaturated ethers and thioethers

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Publication number
GB1394864A
GB1394864A GB2547672A GB2547672A GB1394864A GB 1394864 A GB1394864 A GB 1394864A GB 2547672 A GB2547672 A GB 2547672A GB 2547672 A GB2547672 A GB 2547672A GB 1394864 A GB1394864 A GB 1394864A
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Prior art keywords
carbon atoms
formula
compound
defined above
alkyl
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Expired
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GB2547672A
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Sandoz AG
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Sandoz AG
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Publication date
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1394864A publication Critical patent/GB1394864A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • 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
    • C07C45/673—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 change of size of the carbon skeleton
    • C07C45/676—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 change of size of the carbon skeleton by elimination of carboxyl 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
    • 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
    • C07C45/70—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 reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—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 reaction with functional groups containing oxygen only in singly bound form being hydroxy 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
    • C07C45/72—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 reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1394864 Unsaturated ethers and thioethers SANDOZ Ltd 31 May 1972 [2 June 1971] 25476/72 Heading C2C Compounds of Formula I wherein R 1 is alkyl of 1 to 10 carbon atoms; alkenyl of 3 to 10 carbon atoms; alkynyl of 3 to 10 carbon atoms; cycloalkyl of 3 to 6 carbon atoms; cycloalkyl of 3 to 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms; cycloalkenyl of 5 to 7 carbon atoms; cycloalkenyl of 5 to 7 carbon atoms substituted by alkyl of 1 to 4 carbon atoms; cycloalkyl (of 3 to 6 carbon atoms) alkyl (of 1 to 4 carbon atoms); cycloalkyl (of 3 to 6 carbon atoms) alkyl (of 1 to 4 carbon atoms) ring substituted by alkyl of 1 to 4 carbon atoms; cycloalkenyl (of 5 to 7 carbon atoms) alkyl (of 1 to 4 carbon atoms); or cycloalkenyl (of 5 to 7 carbon atoms) alkyl (of 1 to 4 carbon atoms) ring substituted by alkyl of 1 to 4 carbon atoms; R 2 and R 3 , which are the same or different, are each hydrogen or alkyl of 1 to 4 carbon atoms, Y is cyano; -CONR 4 R 5 wherein R 4 and R 5 , which are the same or different, are each hydrogen of alkyl or 1 to 4 carbon atoms, or R 4 and R 5 together with the nitrogen atom constitute a 5 to 6 membered heterocycle containing either one ring nitrogen atom or one ring nitrogen atom and one ring oxygen atom; -COOR 6 wherein R 6 is alkyl of 1 to 5 carbon atoms; or COR 7 wherein R 7 is alkyl of 1 to 5 carbon atoms; Q is oxygen or sulphur; is or and n is an integer 1, 2 or 3, with the proviso that when Y is -COOR 6 then R 3 is alkyl, are produced by (a) reacting a compound of Formula II wherein R 1 ,R 2 , R 3 , Q, and n are as defined above with a compound of Formula III wherein Y is as defined above and R 8 and R 9 which are the same or different, are each phenyl, alkoxy of 1 to 4 carbon atoms or aryloxy, in the presence of a strong base, or (b) reacting a compound of Formula II with a compound of Formula IV wherein Y is as defined above and R 10 , R 11 and R 12 are each aryl or dialkylamino of 2 to 8 carbon atoms or (c) reacting a compound of Formula V wherein R 1 , R 2 , Q and n are as defined above is or and X is chlorine or bromine, with a compound of Formula VI wherein R 3 and R 7 are as defined above and R 13 is alkyl of 1 to 4 carbon atoms with subsequent acid hydrolysis and dehydration to produce a compound of Formula Ia wherein R 1 , R 2 , R 3 , R 7 , Q, and n are as defined above, or (d) reacting a compound of Formula Ib wherein R 1 , R 2 , R 3 , R 6 , Q, and n are as defined above with a compound of Formula VII MNR 4 R 5 wherein R 4 and R 5 are as defined above and M is hydrogen, lithium or MgBr to produce a compound of Formula Ic wherein R 1 , R 2 , R 3 , R 4 , R 5 , Q, and n are as defined above. The compounds of Formula I are used in insecticidal compositions. The compound of Formula II employed as starting material in processes (a) and (b) above may be produced as follows viz: (a<SP>1</SP>) the compounds of Formula IIa wherein R 1 , R 2 , R 3 , Q and n are as defined above may be produced by reacting a compound of Formula VIII wherein R 1 , R 2 , Q and n are as defined above with a compound of Formula XIII wherein R 3 is as defined above and R 14 is methyl or ethyl, in manner known per se, (b<SP>1</SP>) the compounds of Formula IIb wherein R 1 , R 2 . R 3 Q and n are as defined, above and is or may be produced by etherifying a compound of Formula IX wherein R 1 , R 2 , Q, and n are as defined above, with a compound of Formula X wherein R 3 is as defined above, in manner known per se, (c<SP>1</SP>) the compounds of Formula IIc wherein R 1 , R 2 , R 3 , Q, and n are as defined above, may be produced by reacting a compound of Formula XI wherein R 1 , R 2 , Q, n and X are as defined above. with a compound of Formula XIII with subsequent hydrolysis and decarboxylation, in manner known per se, (d<SP>1</SP>) the compounds of Formula IId wherein R 1 , R 2 , Q and n are as defined above, may be produced by reacting a compound of Formula VIII, with an alkylvinyl ether of 3 to 7 carbon atoms, in the presence of mercuric acetate. The reaction may be effected at elevated temperature and over a prolonged period, e.g. 4 days, with subsequent rearrangement while heating at a temperature of, for example, 160-190‹ C., over a period of, for example, 1 to 2 hours, (e<SP>1</SP>) the compounds of Formula IIe wherein R 1 <SP>1</SP> is alkyl of 1 to 10 carbon atoms; cycloalkyl of 3 to 6 carbon atoms; cycloalkyl of 3 to 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms; cycloalkyl (of 3 to 6 carbon atoms) alkylene (or 1 to 4 carbon atoms); or cycloalkyl (of 3 to 6 carbon atoms) alkyl (of 1 to 4 carbon atoms) ring substituted by alkyl of 1 to 4 carbon atoms; and R 2 , R 3 , Q and n are as defined above, may be produced by catalytic hydrogenation of a compound of Formula IIf wherein R 1 <SP>1</SP>, R 2 , R 3 , Q and n are as defined above, in conventional manner. The compounds of Formula VIII may, for example, be produced by reacting a compound of Formula XII wherein R 1 , 2 R, Q and n are as defined above, with vinyl magnesium chloride or bromide. The compounds of Formulae III, IV, V, VI, VII, IX, X, XI, XII and XIII are either known or may be produced in analogous manner to the process for producing the known compounds.
GB2547672A 1971-06-02 1972-05-31 Unsaturated ethers and thioethers Expired GB1394864A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH803671A CH556311A (en) 1971-06-02 1971-06-02 PROCESS FOR PRODUCING NEW UNSATURED COMPOUNDS.

Publications (1)

Publication Number Publication Date
GB1394864A true GB1394864A (en) 1975-05-21

Family

ID=4334156

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2547672A Expired GB1394864A (en) 1971-06-02 1972-05-31 Unsaturated ethers and thioethers

Country Status (10)

Country Link
BR (1) BR7203543D0 (en)
CH (1) CH556311A (en)
DE (1) DE2226523A1 (en)
ES (1) ES403362A1 (en)
FR (1) FR2140163B1 (en)
GB (1) GB1394864A (en)
IL (1) IL39577A0 (en)
IT (1) IT956090B (en)
SU (1) SU500751A3 (en)
ZA (1) ZA723792B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI865097A (en) * 1985-12-17 1987-06-18 Wellcome Found OIL PESTICID.

Also Published As

Publication number Publication date
BR7203543D0 (en) 1973-05-31
SU500751A3 (en) 1976-01-25
FR2140163A1 (en) 1973-01-12
DE2226523A1 (en) 1972-12-14
CH556311A (en) 1974-11-29
FR2140163B1 (en) 1976-10-29
IT956090B (en) 1973-10-10
ES403362A1 (en) 1975-10-16
IL39577A0 (en) 1972-07-26
ZA723792B (en) 1974-01-30

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees