U.S. patents available from 1976 to present.
U.S. patent applications available from 2005 to present.

Process for the arylation of olefines

Patent 4145362 Issued on March 20, 1979. Estimated Expiration Date: Icon_subject May 10, 1997. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Inventors

Assignee

Application

No. 05/795544 filed on 05/10/1977

US Classes:

558/357, Processes of forming carbon to carbon bond between carbons of two organic reactants546/205, The polycyclo ring system is bicyclo-carbocyclic546/229, Nitrogen attached indirectly to the piperidine ring by nonionic bonding546/230, Cyano attached indirectly to the piperidine ring by nonionic bonding546/232, Chalcogen attached indirectly to the piperidine ring by nonionic bonding546/235, The chalcogen, X, is in a -C(=X)- group546/236, Chalcogen attached indirectly to the piperidine ring by nonionic bonding546/238, The -C(=X)- is part of a -C(=X)X- group, wherein the X's are the same or diverse chalcogens546/239, Plural carbocyclic rings containing546/240, The chalcogen is in an -OH or -OM group (M is Group IA or Group IIA light metal)546/330, Cyano attached indirectly to the six-membered hetero ring by nonionic bonding546/334, Chalcogen attached indirectly to the six-membered hetero ring by nonionic bonding546/335, The chalcogen, X, is part of a -C(=X)X- group, wherein the X's are the same or diverse chalcogens546/338, Acyclic nitrogen bonded directly to chalcogen546/339, Chalcogen attached indirectly to the six-membered hetero ring by nonionic bonding (e.g., sulfato betaines, etc.)546/342, Additional ring containing546/344, The chalcogen is in an -OH or -OM group (M is Group IA or Group IIA light metal)546/346, Halogen attached indirectly to the six-membered hetero ring by nonionic bonding548/578, Benzene ring in a substituent attached to the ring nitrogen of the five membered hetero ring by nonionic bonding549/513, Processes549/557, The chalcogen, X, is part of a -C(=X)X- group or a -X-X- group, wherein the X's are the same or diverse chalcogens (e.g., -COO-HCH-oxirane, etc.)560/103, Monocyclic acid moiety560/254, Aromatic alcohol moiety560/83, Halogen in acid moiety560/9, Sulfur in acid moiety562/459, Aldehyde or ketone562/495, Additional unsaturation564/366, Halogen attached directly or indirectly to the acyclic carbon or chain by acyclic nonionic bonding with no amino nitrogen between the halogen and the aryl ring or ring system564/383, The chain contains carbon to carbon unsaturation568/306, Benzene ring containing568/308, Benzene ring containing568/314, Reactant contains -COO- group568/425, Benzene ring containing568/433, Aldehyde reactant568/655, Halogen containing568/662, Polyoxy568/774, Halogen containing568/812, Halogen containing568/936, Halogen containing570/194Bonding haloalkyl group directly to benzene ring

Examiners

Primary: Torrence, Dolph H.

Attorney, Agent or Firm

International Classes

C07C 49/00 (20060101)
C07C 47/24 (20060101)
C07C 47/20 (20060101)
C07C 49/223 (20060101)
C07C 45/00 (20060101)
C07D 303/08 (20060101)
C07D 303/16 (20060101)
C07D 303/00 (20060101)
C07C 45/69 (20060101)
C07C 205/00 (20060101)
C07C 205/12 (20060101)
C07C 65/00 (20060101)
C07C 17/26 (20060101)
C07C 17/00 (20060101)
C07C 65/32 (20060101)

Foreign Application Priority Data

1969-04-10 BE

Abstract

A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.

Other References

  • Fieser et al., J. Am. Chem. Soc., vol. 60, pp. 1142-1144 (1938)
  • Muller, Angew. Chem., vol. 61, pp. 179-183 (1949)
  • Kozlov, J. General Chem., USSR, vol. 31, pp. 2059-2063 (1960)
  • Dombrovskii et al., Chem. Abst., vol. 51, 7337, 8038 (1957)
  • USSR patent 187,034, Chem. Abst., vol. 67, 73335 (1967)
  • Malinowski et al., Chem. Abst., vol. 49, 1034-1035 (1955)
  • Brunner et al., Chem. Abst., vol. 44, 1054g (1950)
  • Organic Reactions II, pp. 189-260 (1960)
  • Houben-Weyl "Methoden der Organischen Chemie" (1965), Part 10/3, pp. 25, 26, 28, 30, 31, 172, 173
  • Koelsch, J. Am. Chem. Soc., vol. 65, pp. 57-58 (1943)
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