• Refine Query
  • Source
  • Publication year
  • to
  • Language
  • 1
  • Tagged with
  • 1
  • 1
  • 1
  • 1
  • 1
  • 1
  • 1
  • About
  • The Global ETD Search service is a free service for researchers to find electronic theses and dissertations. This service is provided by the Networked Digital Library of Theses and Dissertations.
    Our metadata is collected from universities around the world. If you manage a university/consortium/country archive and want to be added, details can be found on the NDLTD website.
1

The prepration of some unsymmetrical ortho substituted ̲o-dibenzoylbenzenes and 1,3-diphenylisobenzofurans

Spangler, Martin Ord Lee 07 April 2010 (has links)
A review of the more important methods of synthesis of 1,3-diarylisobenzofurans (III) and o-diaroylbenzenes (II) was made. These were compared with the possibilities involved in the type of synthesis in which substituted o-benzylbenzophenones (I) are oxidized to o-diaroylbenzenes (II) and subsequently reduced to 1,3-diarylisobenzofurans (III). It is seen that this latter method affords a greater variety of substituents for these types of compounds than the other methods. The possible orientations of substituents are also greater. Two o-benzylbenzophenones (I), 2’-methyl-2-benzylbenzophenone (LIII) and 2'-methoxy-2-benzylbenzophenone (LVI), were prepared by the action of the appropriate Grignard reagent on o-benzylbenzonitrile (LII) and subsequent hydrolysis of the intermediate ketimine. These were oxidized to the corresponding o-dibenzoylbenzenes (II), 2’-methyl-2-benzoy1 benzophenone (LIV), and 2'-methoxy-2- benzoylbenzophenone (LVII), by the use of sodium dichromate and sulfuric acid, Reduction of these with zinc dust in acetic acid gave the corresponding 1,3-diarylisobenzofurans (III), 1-(2‘-methylpheny1)-3-phenylisobenzofuran (LV) and 1-2" -methoxyphenyl)-3-phenyl isobenzofuran (LVIII). Attempts were made to prepare 2'-chloro-2-benzylbenzophenone (I; Reo-Cl and R'=R) by the same method as that in the above-mentioned paragraph. None of the ketone could be obtained. A small amount of a hydrocarbon was obtained in one case which was analyzed as C₂₀H₁₄. The action of the Grignard reagent of 4-iodo-1, 3-dimethylbenzene on o-chlorobenzaldehyde gave 2-chloro-2', 4'-dimethylbenzohydrol (LI). New compounds synthesized are 2‘-methy1-2~benzoylbenzophenone (LIV), 2'-methoxy-2-benzoyl benzophenone (LVII), 1-(2'-methylphenyl)-3-phenylisobenzofuran (LV), 1-(2'-methoxyphenyl1)-3-phenylisobenzofuran (LVIII), and 2-chloro-2! ,4'-dimethylbenzohydrol (LI). / Master of Science

Page generated in 0.0386 seconds