GB666713A - Manufacture of new spirans - Google Patents

Manufacture of new spirans

Info

Publication number
GB666713A
GB666713A GB4048/49A GB404849A GB666713A GB 666713 A GB666713 A GB 666713A GB 4048/49 A GB4048/49 A GB 4048/49A GB 404849 A GB404849 A GB 404849A GB 666713 A GB666713 A GB 666713A
Authority
GB
United Kingdom
Prior art keywords
spiran
propionic acid
chloride
keto
acid chloride
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
Application number
GB4048/49A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB666713A publication Critical patent/GB666713A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • 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
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/74—Acyl halides containing six-membered aromatic rings and other rings

Landscapes

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

Abstract

1 : 11 - (Hydrodinaphthyl - 8 : 81) - spirans containing the nucleus of the formula <FORM:0666713/IV (b)/1> and containing a keto group in one or both of the 4- and 41-positions (with or without further substituents, e.g. a substituted amino group or a halogen atom in one or both of the 5- and 51- positions, or also alkyl or aryl groups, and with or without further fused-on rings), are manufactured by the action of an agent capable of bringing about ring closure on a fluorene derivative of the general formula <FORM:0666713/IV (b)/2> wherein the carbon atom C1 either forms with a vicinal benzene nucleus part of a partially hydrogenated naphthalene nucleus and carries a hydrocarbon residue substituted in the b -position by a - <FORM:0666713/IV (b)/3> group (R being a hydroxy group or a halogen atom), or carries two residues of the said kind. Such starting materials may be hydrogenated fluoranthenes (e.g. 1 : 2-dihydro- or 1 : 2 : 3 : 4-tetrahydrofluoranthenes), fluorenes, benzofluorenes, naphthofluorenes or 4 : 5-methylenephenanthrenes (4 : 5-vinylenefluorenes) or their nuclear substitution products. The reaction may be carried out in the presence or absence of a solvent (e.g. benzene, carbon disulphide, petroleum ether or ligroin), suitable ring-closing agents being substances of electrophilic character such as aluminium chloride, zinc chloride, stannic chloride, boron trifluoride or mixtures thereof, or concentrated inorganic acids or their anhydrides, e.g. sulphuric, phosphoric or hydrobromic acid, or phosphorus pentoxide, or mixtures thereof. Examples describe the preparation of: (1) and (4) 1 : 11 - (4 : 41 - diketo - 1 : 2 : 3 : 4 : 11 : 21 : 31 : 41 - octahydrodinaphthyl-8 : 81) - spiran from b : b 1 - (fluorenylidene - 9 : 9)-bis-propionic acid chloride or from b -(4-keto - 1 : 2 : 3 : 4 - tetrahydrofluoranthenyl-1)-propionic acid chloride; (2) 1 : 11 - (4-keto - 1 : 2 : 3 : 4 : 11 : 21 : 31 : 41 - octahydrodinaphthyl - 8 : 81) - spiran from b - (1 : 2 : 3 : 4 - tetrahydrofluoranthenyl - 1) - propionic acid chloride; (3) 1 : 11-(2 : 2 : 4-trimethyl-41-keto-1 : 2 : 11 : 21 : 31 : 41 - hexahydrodinaphthyl - 8 : 81)-spiran from b -(2 : 2 : 4-trimethyl-1 : 2-dihydrofluoranthenyl - 1) - propionic acid chloride; (5) 1 : 11-(4 : 41-diketo-7 : 71-vinylene-1 : 2 : 3 : 4 : 11 : 21 : 31 : 41 - octahydrodinaphthyl-8 : 81)-spiran from b : b 1-(4 : 5-vinylenefluorenylidene-9 : 9)-bis-propionic acid chloride; (6) 1 : 11-(3-methyl-4-keto - 1 : 2 : 3 : 4 : 11 : 21 : 31 : 41-oxtahydrodinaphthyl - 8 : 81) - spiran from b - (1 : 2 : 3 : 4 - tetrahydrofluoranthenyl - 1) - a - methylpropionic acid chloride. Fluorene derivatives of the second general formula above are obtainable by converting into carboxylic acids or acid halides (e.g. chlorides) the corresponding nitriles obtained by reacting the appropriate fluorene or hydrogenated fluoranthene compound with an acrylic acid nitrile, e.g. 1 : 2 : 3 : 4-tetrahydrofluoranthene, 2 : 2 : 4 - trimethyl - 1 : 2 - dihydrofluoranthene or 4 : 5 - vinylenefluorene with acrylonitrile, or 1 : 2 : 3 : 4-tetrahydrofluoranthene with methacrylonitrile. Alternatively an alkali compound of a fluorene or fluoranthene may be condensed with an organic halogen compound containing the desired b -substituent. b - (4 - Keto - 1 : 2 : 3 : 4 - tetrahydrofluoranthenyl-1)-propionic acid chloride is prepared by the action of thionyl chloride on the corresponding acid obtained as a by-product in the saponification of 9 : 9-di-(b -cyanoethyl)-fluorene for the production of the bis-propionic acid. A sample has been furnished under Sect. 2 (5) of 1 : 11 - (4 : 41 - diketo - 5 : 51 - dibromo - 1 : 2 : 3 : 4 : 11 : 21 : 31 : 41 - octahydrodinaphthyl-8 : 81)-spiran, prepared from b : b 1-(2 : 7-dibromofluorenylidene - 9 : 9) - bis - propionic acid chloride, which is obtainable from the corresponding dinitrile produced by condensing 2 : 7-dibromofluorene with two molecular proportions of acrylonitrile. The Specification as open to inspection under Sect. 91 comprises generally the manufacture of any compounds containing the spiran structure shown in the first general formula above from compounds of the second general formula above in which the carbon atom C1 carries any residue (or residues) capable of condensing with the vicinal benzene nucleus to form a partially hydrogenated naphthalene nucleus. In particular, in the production of the ketonic compounds defined above, the starting materials defined above may be replaced by compounds (likewise obtainable from the corresponding nitriles) containing ester groups, or carbonyl (aldehyde or acyl) or functionally converted carbonyl groups in place of the carboxyl or acid halide groups. This subject-matter does not appear in the Specification as accepted.
GB4048/49A 1948-02-13 1949-02-14 Manufacture of new spirans Expired GB666713A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH666713X 1948-02-13

Publications (1)

Publication Number Publication Date
GB666713A true GB666713A (en) 1952-02-20

Family

ID=4527344

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4048/49A Expired GB666713A (en) 1948-02-13 1949-02-14 Manufacture of new spirans

Country Status (1)

Country Link
GB (1) GB666713A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101437865B (en) * 2004-11-03 2013-03-20 住友化学株式会社 Class of bridged biphenylene polymers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101437865B (en) * 2004-11-03 2013-03-20 住友化学株式会社 Class of bridged biphenylene polymers

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