GB1082808A - Cyclobutanes - Google Patents
CyclobutanesInfo
- Publication number
- GB1082808A GB1082808A GB47839/64A GB4783964A GB1082808A GB 1082808 A GB1082808 A GB 1082808A GB 47839/64 A GB47839/64 A GB 47839/64A GB 4783964 A GB4783964 A GB 4783964A GB 1082808 A GB1082808 A GB 1082808A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- butyl
- ethyl
- cyclobutanone
- substituents
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/20—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds unconjugated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
As co-monomers in the manufacture of fibre- and film-forming polymers, use is made of cyclobutanone or cyclobutanol derivatives of either of the formulae <FORM:1082808/C3/1> or <FORM:1082808/C3/2> in which the substituents R2, taken singly, are alkyl groups of 1-8 carbon atoms or, taken collectively with the carbon atom to which they are attached, denote a saturated carbocyclic ring of 4-8 carbon atoms, each of the substituents R3 may be hydrogen or a halogen atom or an alkyl group of 1-8 carbon atoms and the substituents R4, taken singly, may be hydrogen or halogen atoms or alkyl groups of 1-8 carbon atoms or, taken collectively with the carbon atoms to which they are attached, denote an unsaturated carbocyclic ring of 4-8 carbon atoms (see Division C2). Thus, the compounds may be co-polymerized with one or more polymerizable vinyl monomers or the cyclobutanols may be esterified with dicarboxylic acids to yield difunctional monomers useful for cross-linking resins. Examples are given of the polymerization in aqueous medium of 2 - butyl - 2 - ethyl - 3 - vinylcyclobutanol and 2 - butyl - 2 - ethyl - 3 - vinylcyclobutanone with acrylonitrile in the presence of sodium lauryl sulphate and ammonium persulphate. The polymers obtained can be spun into fibres from dimethylformamide solutions.ALSO:The invention comprises compounds of the formula <FORM:1082808/C2/1> in which the substituents R2, taken singly, are alkyl groups of 1-8 carbon atoms or, taken collectively with the carbon atom to which they are attached, denote a saturated carbocyclic ring of 4-8 carbon atoms, each of the substituents R3 may be hydrogen or a halogen atom or an alkyl group of 1-8 carbon atoms and the substituents R4, taken singly, may be hydrogen or halogen atoms or alkyl groups of 1-8 carbon atoms or, taken collectively with the carbon atoms to which they are attached, denote an unsaturated carbocyclic ring of 4-8 carbon atoms. The compounds are obtainable by reacting a dialkyl ketene with a conjugated diene. Suitable dialkyl ketenes include dimethylketene, dipropylketene, dioctylketene, pentamethyleneketene, ethylbutylketene and di(2-ethylhexyl)ketene. Suitable conjugated dienes include 1,3-butadiene, isoprene, piperylene, vinyl-1-cyclohexene, chloroprene, propenyl-1-cyclo-octene and 2-(tert.-butyl)-1,3-butadiene. In typical examples, (1) butylethylketene and 1,3 - butadiene yield 2 - butyl - 2 - ethyl - 3-vinylcyclobutanone and, as a by-product, 2,4-dibutyl - 2,4 - diethyl - 1,3 - cyclobutanedione, (2) butylethylketene and isoprene yield a mixture of isomeric 3-substituted-2-butyl-2-ethylcyclobutanones, and (3) ethylisobutyl-ketene and chloroprene yield 2-ethyl-2-isobutyl-3-(1-chlorovinyl)cyclobutanone. Other specified products include 2,2-dibutyl-3-(2-methylpropenyl)-cyclobutanone, 2 - butyl - 2 - ethyl - 3 - (1-cyclohexenyl)cyclobutanone and 1-oxo-3-vinylspiro-(3,5)-nonane. The invention also comprises products of the formula <FORM:1082808/C2/2> in which R2, R3 and R4 are as specified above. These compounds are obtainable by treating a compound of the first formula above with a reagent which reduces the keto group but does not reduce the double bond. Specified reducing agents of this kind are metal hydrides, e.g. lithium hydride, lithium aluminium hydride or sodium or potassium borohydride, aluminium alkoxides, e.g. aluminium isopropoxide, and metallic sodium in ethanol. Examples are given of the reduction of 2-butyl-2-ethyl-3-vinylcyclobutanone, 2 - ethyl - 2 - butyl - 3-propenylcyclobutanone, 2 - ethyl - 2 - isobutyl-3 - (1 - chlorovinyl)cyclobutanone and 2,2-dibutyl - 3 - (1 - butenyl)cyclobutanone with lithium aluminium hydride. The products are useful as comonomers in the preparation of copolymers (see Division C3).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US32626763A | 1963-11-26 | 1963-11-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1082808A true GB1082808A (en) | 1967-09-13 |
Family
ID=23271505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB47839/64A Expired GB1082808A (en) | 1963-11-26 | 1964-11-25 | Cyclobutanes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1082808A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4284821A (en) | 1977-11-24 | 1981-08-18 | Ciba-Geigy Corporation | Dichlorovinylcyclobutanones, processes for preparing them, and their use as intermediates for producing pesticidal compositions |
-
1964
- 1964-11-25 GB GB47839/64A patent/GB1082808A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4284821A (en) | 1977-11-24 | 1981-08-18 | Ciba-Geigy Corporation | Dichlorovinylcyclobutanones, processes for preparing them, and their use as intermediates for producing pesticidal compositions |
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