FR2252323A1 - 2,3-Disubstd cycloalkanones prepn - by reacting cycloalk-2-en-1-ones with organo-copper-lithium cpds - Google Patents

2,3-Disubstd cycloalkanones prepn - by reacting cycloalk-2-en-1-ones with organo-copper-lithium cpds

Info

Publication number
FR2252323A1
FR2252323A1 FR7438463A FR7438463A FR2252323A1 FR 2252323 A1 FR2252323 A1 FR 2252323A1 FR 7438463 A FR7438463 A FR 7438463A FR 7438463 A FR7438463 A FR 7438463A FR 2252323 A1 FR2252323 A1 FR 2252323A1
Authority
FR
France
Prior art keywords
reacting
formula
organo
lithium
cpd
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Withdrawn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
FR7438463A
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.)
Teijin Ltd
Original Assignee
Teijin 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 JP13069673A external-priority patent/JPS5318494B2/ja
Priority claimed from JP854174A external-priority patent/JPS5614651B2/ja
Application filed by Teijin Ltd filed Critical Teijin Ltd
Publication of FR2252323A1 publication Critical patent/FR2252323A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • 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
    • 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
    • C07C45/69—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
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
    • 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
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings

Landscapes

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

Abstract

Cycloalkanone derivs. of formula (Ia) or (Ib): (where R1-R8 are H or monovalent organic residues (pref. 1-20C alkyl, cycloalkyl, alkenyl, alkynyl or aryl), or 2 of these groups may be linked so as to form a ring, and RA and RB are monovalent organic groups (pref. 1-20C organic groups)), e.g. 2-allyl-3-methyl-cyclohexanone, are prepd. by (a) reacting cycloalkenones of formula (IIa) or (IIb) with organo-copper-lithium cpd. of the formula Cu(RB)nLi-Y2-n (III) where n is 1 or 2, the residues RB being identical or different when n is 2; and Y is a monovalent anion) or with a complex of (III) and a trivalent organophosphorus cpd. in the presence of an inert aprotic organic medium and (b) reacting the product with a cpd. of the formula RAX (IV) (where X is halogen) in the presence of an N- or S-contg. polar aprotic organic solvent. Reactions (a) and (b) are pref. carried out at -78 to +50 degrees C. (Ia) and (Ib) are useful as pharmaceuticals, agricultural chemicals, perfumes, and intermediates for products such as steroids, terpenoids, prostaglandins, jasmones or pyrethroids.
FR7438463A 1973-11-22 1974-11-22 2,3-Disubstd cycloalkanones prepn - by reacting cycloalk-2-en-1-ones with organo-copper-lithium cpds Withdrawn FR2252323A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP13069673A JPS5318494B2 (en) 1973-11-22 1973-11-22
JP854174A JPS5614651B2 (en) 1974-01-21 1974-01-21

Publications (1)

Publication Number Publication Date
FR2252323A1 true FR2252323A1 (en) 1975-06-20

Family

ID=26343077

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7438463A Withdrawn FR2252323A1 (en) 1973-11-22 1974-11-22 2,3-Disubstd cycloalkanones prepn - by reacting cycloalk-2-en-1-ones with organo-copper-lithium cpds

Country Status (6)

Country Link
DE (1) DE2455444A1 (en)
DK (1) DK606474A (en)
FR (1) FR2252323A1 (en)
NL (1) NL7415280A (en)
NO (1) NO744186L (en)
SE (1) SE7414648L (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0019475A2 (en) * 1979-05-18 1980-11-26 Teijin Limited Process for preparing adjacently disubstituted ketones, novel prostaglandins E1 and anti-thrombotic compositions containing them

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR9707235A (en) * 1996-01-31 1999-12-28 Nippon Kayaku Kk Pharmaceutical composition, compound 2,3-disubstituted cyclopentanone derivative, processes for the production of a 2,3-disubstituted cyclopentanone derivative, from an acid (1r, 2s) -2-[ (2r) - (2 - protected or unprotected amino-2-carboxy)ethylthio]methyl-3-oxo-1-carboxylic cyclopentane or an alkyl ester thereof or a pharmacologically acceptable salt thereof, cyclopentanone derivative compound (2s, 3r) - 3- protected hydroxymethyl-2-thiomethyl, and, accelerator of neuron differentiation.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0019475A2 (en) * 1979-05-18 1980-11-26 Teijin Limited Process for preparing adjacently disubstituted ketones, novel prostaglandins E1 and anti-thrombotic compositions containing them
EP0019475A3 (en) * 1979-05-18 1981-02-11 Teijin Limited Process for preparing adjacently disubstituted ketones, novel prostaglandins e1 and anti-thrombotic compositions containing them

Also Published As

Publication number Publication date
SE7414648L (en) 1975-05-23
NO744186L (en) 1975-06-16
NL7415280A (en) 1975-05-26
DK606474A (en) 1975-07-21
DE2455444A1 (en) 1975-05-28

Similar Documents

Publication Publication Date Title
Brown et al. Organometallic models for possible Fischer-Tropsch intermediates. Synthesis, structure, and reactions of a formaldehyde complex of osmium
Corey et al. Introduction of two carbon appendages at a carbonyl carbon. Application to double chain branching and spiro annulation operations
Carbonaro et al. Oligomerization catalysts. III. Cyclocodimerization of conjugated dienes with acetylenic hydrocarbons catalyzed by iron (0) complexes. Synthesis of 1, 2-diphenyl-1, 4-cyclohexadiene
Tanaka et al. Asymmetric hydrogenation by a chiral diphosphinite rhodium complex
GB977108A (en) Process of co-oligomerisation
FR2252323A1 (en) 2,3-Disubstd cycloalkanones prepn - by reacting cycloalk-2-en-1-ones with organo-copper-lithium cpds
Otsuka et al. Catalytic oxidation of isocyanides: a nickel–oxygen complex
Yamamoto et al. Insertion of Isonitrile into Alkyl-Nickel Bonds
DE2350689C2 (en) Process for the dimerization or codimerization of certain diolefins and catalyst for carrying out this process
Atkinson et al. Stereospecific addition of an amino-nitrene to mono-and di-enes
Kasahara et al. Synthesis of a New δ-Bonded Dimethyl Rhodium Derivative, π-C 5 H 5 Rh (CH 3) 2 [P (C 6 H 5) 3]
CA1082720A (en) Method of preparing transition metal-olefin complex compounds and alkali metal-transition metal-olefin complex compounds
GB1361018A (en) Process for the production of aliphatic carboxylic acid chlorides
Hidai et al. Synthesis of (+)-or (–)-citronellol from isoprene
Negishi et al. A novel regiospecific aryl ketone synthesis by the reaction of arylborate anions with acyl chlorides
Green et al. The synthesis and some reactions of bis (acetonitrile)(diene)-rhodium and-iridium tetrafluoroborate
Tsutsui et al. PI-SIGMA REARRANGEMENTS OF PI-CYCLOPENTADIENYL GROUP: REACTION OF TITANOCENE DICHLORIDE WITH DIMETHYLSULFOXIDE
BERKE DICARBONYLDI-TERT-BUTYLALLENYLIDENECYCLOPENTADIENYL MANGANESE
US2672461A (en) Preparation of 2-phenyl-3-pyridol from 2-benzoylfuran
SU483395A1 (en) The method of obtaining s-nitrosoarylamines
ES430076A1 (en) 4-Oxa-5-hydroxypolycycloalkenones-(3)
Zelonka et al. Tertiary phosphine and arsine complexes of copper (II)
SU371248A1 (en) Method of producing 2-methyleneoxyphenylferrocenyl
Hoshi et al. Synthesis of S-alkyl alkanethioates via 1-iodoalk-1-enyldialkylboranes
Grigg et al. A three-stage synthesis of a nickel corrin perchlorate from pyrrolic intermediates

Legal Events

Date Code Title Description
ST Notification of lapse