Hart et al., 1974 - Google Patents
Possible photochemical (. pi. 4s+. pi. 2a) Diels-Alder reaction. Photodimerization of 6, 6-dimethyl-2, 3-benzo-2, 4-cycloheptadienoneHart et al., 1974
- Document ID
- 10102697242767084489
- Author
- Hart H
- Miyashi T
- Buchanan D
- Sasson S
- Publication year
- Publication venue
- Journal of the American Chemical Society
External Links
Snippet
Irradiation of the title compound 11 gave predominantly two stereoisomeric dimers, shown by chemical and X-ray crystal data to have the structures 16 and 17, together with a small amount of a cyclobutane dimer (19?). A mechanism which rationalizes the major products …
- 238000005698 Diels-Alder reaction 0 title abstract description 8
Classifications
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or 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
- C07C45/512—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 a free 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2103/00—Systems containing at least three condensed rings
- C07C2103/02—Ortho- or ortho- and peri-condensed systems
- C07C2103/04—Ortho- or ortho- and peri-condensed systems containing three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- 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
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2102/00—Systems containing two condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having -CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
Similar Documents
Publication | Publication Date | Title |
---|---|---|
White et al. | The total synthesis of. alpha.-and. beta.-Bourbonene | |
Das et al. | Total synthesis of steroids. Part 1. Ring A aromatic compounds. Regiocontrol in diene additions with 6-methoxy-1-vinyl-3, 4-dihydronaphthalene | |
Swenton et al. | Spiro-fused 2, 5-cyclohexadienones from thermal 1, 3-shifts in quinol vinyl ethers. Reactions in nonbenzenoid systems and limitations of the chemistry | |
Hayakawa et al. | Carbon-carbon bond formation promoted by transition metal carbonyls. 20. Iron carbonyl promoted reaction of. alpha.,. alpha.'-dibromo ketones and aromatic olefins leading to 3-arylcyclopentanones. The [3+ 2] cycloaddition involving an allylic cation | |
Evans et al. | Total synthesis of naturally occurring substances. II. The synthesis of the hasubanan carbocyclic system | |
Schaefer et al. | Selenium dioxide oxidations. III. Oxidation of olefins | |
Paquette et al. | Synthetic studies relating to the structure of senoxydene. A sequential annulation approach to angular triquinane construction capable of varied tetramethyl substitution patterns | |
Hart et al. | Possible photochemical (. pi. 4s+. pi. 2a) Diels-Alder reaction. Photodimerization of 6, 6-dimethyl-2, 3-benzo-2, 4-cycloheptadienone | |
Schuster et al. | Mechanism of photoisomerization of cyclohexenones. 10-Hydroxymethyl-. DELTA. 1, 9-2-octalone. Question of hydrogen abstraction from benzene by ketone triplets | |
Herz et al. | Resin acids. XIX. Structure and stereochemistry of adducts of levopimaric acid with cyclopentenone and 1-cyclopentene-3, 5-dione. Fovarski reaction of an enedione epoxide | |
Fuson et al. | Vinyl Alcohols. XVIII. 1 Increased Hindrance | |
Hart et al. | Stereochemistry of the photoinduced and Michael addition of methanol to seven-and eight-membered 2-cycloalkenones | |
Thummel et al. | Aromatization of 1, 4-dihydrobenzocycloalkenes, 1, 4-dihydronaphthocycloalkenes, and related systems | |
Hart et al. | Stereochemistry of the photoinduced and Michael addition of methanol to seven-and eight-membered 2-cycloalkenones. The effect of methyl substituents | |
Noyori et al. | Photochemistry of 2, 6-cycloheptadienones in strong acid. Protonated version of cycloheptadienone-oxyheptatrienyl transformation | |
Dauben et al. | Solvolysis of bicyclo [2.1. 0] pentanyl-1-methyl p-nitro-benzoate | |
Ireland et al. | Total synthesis of terpenes. XIV. Interpretation of the transmogrification of 4. beta., 7a. alpha.-dimethyl-1. alpha.-hydroxy-4. alpha.-phenyl-4, 5, 6, 7-tetrahydro-2-indanone by base | |
Johnson et al. | Steroid Total Synthesis—Hydrochrysene Approach. II. 1 1-Methoxy-8-keto-10a-methyl-5, 6, 8, 9, 10, 10a, 11, 12-octahydrochrysene | |
Harding et al. | Nonenzymic Biogenetic-like Olefinic Cyclizations. Cyclization of 4-(trans-3, 7-octadienyl)-3-methyl-2-cyclohexen-1-ol and 4-(trans, trans-7-methyl-3, 7, 11-dodecatrienyl)-3-methyl-2-cyclohexen-1-ol | |
Lokensgard et al. | Decomposition of. beta.,. gamma.-unsaturated diazoketone. Evidence for the intermediacy of a bicyclopentanone | |
Rao et al. | A stereospecific synthesis of (±)-ferruginol | |
Kiefer et al. | Oxidation of arylpropenes by 2, 3-dichloro-5, 6-dicyanoquinone | |
Schuster et al. | Photochemical Transformations of 2, 2-Dimethylspiro [4, 5] deca-6, 9-dien-8-one. Solvent Effects on the Stereochemistry of the Lumiketone Rearrangement | |
Gutsche et al. | The photolysis of bicyclo [5.2. 1] decan-10-ones | |
Overman et al. | Preparation of substituted 2-pyridones by thermal rearrangement of propargylic pseudoureas. Improvements in the 2-pyridone yields by variations of the pseudourea NR2 substituent |