Part I. Dibenzcycloheptatrienes. Part 2. A New Molecular Rearrangement Effected by Aluminium Chloride

Razdan, Raj Kumar (1954) Part I. Dibenzcycloheptatrienes. Part 2. A New Molecular Rearrangement Effected by Aluminium Chloride. PhD thesis, University of Glasgow.

Abstract

A: Dibenzcycloheptatrienes. 2:3-Dimethoxy-9-and -10-mefhylphenanthrenes were synthesised and, by expansion of the central ring in each, were converted into dihenzocycloheptatrienones. Thereby 13:14-dimethoxy-3:4-5:6-dihenzocyclohepta-1:3:5-triene was isolated and fully characterised hut the isomeric triene was less well defined and attempted interconversion of the two gave results which were not free of ambiguity. B: A New Molecular Rearrangement effected by Aluminium Chloride. It is shown that through being heated with aluminium chloride chromanone is rearranged to 7-hydroxyindanone and dihydrocoumarin to 4-hydroxyindanone. Further applications of this type of rearrangement are described and discussed. In particular it is employed to prepare 6-hydroxyperinaphthen-7-one, the corresponding 8:9-dihydride and 6-hydroxy-perinaphthen-9-one. A comparative study of these three compounds is made to evaluate the chemical effects which are associated with the strong hydrogen-bonding present in the first of them. An improved method for the synthesis of chromanones has been developed.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1954
• Depositing User: Enlighten Team
• Unique ID: glathesis:1954-79096
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Mar 2020 11:43
• Last Modified: 05 Mar 2020 11:43
• URI: https://theses.gla.ac.uk/id/eprint/79096