DE1618656A1 - Neue ungesaettigte Cyclobutanderivate und Verfahren zu ihrer Herstellung - Google Patents
Neue ungesaettigte Cyclobutanderivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1618656A1 DE1618656A1 DE19671618656 DE1618656A DE1618656A1 DE 1618656 A1 DE1618656 A1 DE 1618656A1 DE 19671618656 DE19671618656 DE 19671618656 DE 1618656 A DE1618656 A DE 1618656A DE 1618656 A1 DE1618656 A1 DE 1618656A1
- Authority
- DE
- Germany
- Prior art keywords
- trans
- hexadiene
- sensitizer
- preparation
- vinyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 6
- 239000012965 benzophenone Substances 0.000 claims description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 claims 1
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 claims 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 claims 1
- BDJAEZRIGNCQBZ-UHFFFAOYSA-N methyl-cyclobutane Natural products CC1CCC1 BDJAEZRIGNCQBZ-UHFFFAOYSA-N 0.000 claims 1
- 150000004002 naphthaldehydes Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 230000010355 oscillation Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical class C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001930 cyclobutanes Chemical class 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- -1 alkenyl cyclobutane compounds Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/06—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
- C07C2/44—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion of conjugated dienes only
-
- 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)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1483466 | 1966-02-24 | ||
| IT428466 | 1966-02-24 | ||
| IT1429166 | 1966-06-22 | ||
| IT1933166 | 1966-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618656A1 true DE1618656A1 (de) | 1971-04-01 |
Family
ID=27452679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618656 Pending DE1618656A1 (de) | 1966-02-24 | 1967-02-23 | Neue ungesaettigte Cyclobutanderivate und Verfahren zu ihrer Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1618656A1 (en:Method) |
| FR (1) | FR1511975A (en:Method) |
| GB (1) | GB1155926A (en:Method) |
| NL (2) | NL6702400A (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643063B1 (de) * | 1967-04-08 | 1972-03-16 | Studiengesellschaft Kohle Mbh | Verfahren zur Cyclodimerisation von 1,3-Diolefinen mittels Nickel enthaltender Katalysatoren |
| EP0966457A1 (en) * | 1997-03-14 | 1999-12-29 | Sepracor, Inc. | Ring opening metathesis of alkenes |
-
1967
- 1967-02-17 NL NL6702400A patent/NL6702400A/xx unknown
- 1967-02-17 NL NL6702399A patent/NL6702399A/xx unknown
- 1967-02-20 FR FR95614A patent/FR1511975A/fr not_active Expired
- 1967-02-20 GB GB7894/67A patent/GB1155926A/en not_active Expired
- 1967-02-23 DE DE19671618656 patent/DE1618656A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643063B1 (de) * | 1967-04-08 | 1972-03-16 | Studiengesellschaft Kohle Mbh | Verfahren zur Cyclodimerisation von 1,3-Diolefinen mittels Nickel enthaltender Katalysatoren |
| EP0966457A1 (en) * | 1997-03-14 | 1999-12-29 | Sepracor, Inc. | Ring opening metathesis of alkenes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1155926A (en) | 1969-06-25 |
| FR1511975A (fr) | 1968-02-02 |
| NL6702399A (en:Method) | 1967-08-25 |
| NL6702400A (en:Method) | 1967-12-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Blomquist et al. | Many-membered carbon rings. V. cyclodecyne, cis-and trans-cyclodecene and related compounds1 | |
| DE2718549A1 (de) | Neue riechstoffe | |
| Brace | Cyclization reactions of perfluoroalkyl-substituted radicals | |
| DE69527045T2 (de) | Tetrahydrofurane und tetrahydropyrane | |
| Jones et al. | Alkaloids of the ant Chelaner antarcticus | |
| DE1618656A1 (de) | Neue ungesaettigte Cyclobutanderivate und Verfahren zu ihrer Herstellung | |
| CA1042469A (en) | Process for producing alcohols | |
| CH657868A5 (de) | Cyclohexanolderivate enthaltende duftstoffmischungen. | |
| DE2833283A1 (de) | Norbornan- und norbornen-verbindungen und herstellungsverfahren | |
| Gilman et al. | The Preparation and Rearrangement of 2-Allyl-1, 2-dihydroquinoline | |
| EP0012224B1 (de) | Verfahren zur Herstellung von Riechstoffgemischen | |
| Spangler et al. | Synthesis and characterization of representative octa-1, 3, 5, 7-tetraenes and deca-1, 3, 5, 7, 9-pentaenes | |
| Rosowsky et al. | Synthesis and Properties of Bicyclic Oxetanes1 | |
| DE1818048C2 (de) | Verfahren zur Herstellung von 5-Isopropyliden-2-norbornen durch Isomerisieren von 5-Isopropenyl-2-norbornen | |
| CH642935A5 (de) | Verfahren zur herstellung von 2,3-dimethylbuten-2. | |
| Wheeler et al. | Bicyclic ketones. I. Decomposition of terpene ketone tosylhydrazones | |
| DE3242042C1 (de) | Gemisch von Dimethyl-tricyclo[5.2.1.0?]decan-Derivaten sowie dessen Herstellung und Verwendung als Riech- und Aromastoff | |
| DE2856721C2 (de) | Verfahren zur Herstellung von 2-Methyl-4-(1-methyläthyl)-3-cyclohexen-1-on | |
| Schuster et al. | The Photolysis of 7-Ketonorbornene1 | |
| DE2235466C3 (de) | 3-Phenylpropanale und 4-Phenylbutanale sowie ein Verfahren zu deren Herstellung | |
| DE1493037A1 (de) | Verfahren zur Herstellung polycyclischer Verbindungen | |
| DE1230793B (de) | Verfahren zur Herstellung von 1-Vinyl-2-alkenylcyclobutanen | |
| DE1493752A1 (de) | Verfahren zur Herstellung von reinem wasserfreiem 2-Amino-propionitril | |
| DE69020453T2 (de) | Verfahren zur Herstellung von alpha,beta-ungesättigtem Aldehyd. | |
| DE2102953C2 (de) | Trien-Kohlenwasserstoffe mit 2 konjugierten Doppelbindungen |