Some Investigations on Aromatic Structures: (1) Studies in Tropolone Chemistry (2) Synthesis of 4:5-Dimethylphenanthrene

Scott, Alastair I (1952) Some Investigations on Aromatic Structures: (1) Studies in Tropolone Chemistry (2) Synthesis of 4:5-Dimethylphenanthrene. PhD thesis, University of Glasgow.

Abstract

By extension of the method of preparing tropolone by bromination - debydrobromination of oycloheptane-1:2-dione to isopropylcycloheptanediones, alpha-, beta-, and gamma- isopropyltropolones have been prepared and have been shown to be identical with the naturally-occurring alpha-, beta-, and gamma thujaplicins. Some reactions of tropolone have been examined, in particular, the Friedel-Crafts and Reimer-Tiemann reactions. The reduction of tropolone with lithium aluminium hydride has been studied. In the course of an attempt to prepare a gamma-nitrotropolone, cyclodecane-1:2-dione was found to dimerise. The nature of this product has been examined and a structure proposed. An attempted synthesis of gamma-tropolone is also described. PART II. 4:5-Dimethylphenanthrene has been prepared from pyrene by a series of smooth reactions. Ozonolysis of pyrene gave 4-formylphenanthrene-5-carboxylic acid which was reduced to 4:5-bis-hydroxymethyIphenanthrene. Replacement of the hydroxyl groups with bromine followed by the formation of phenanthrene-4:5-diisothioronium dibromide led to the production of 4:5-dimethylphenanthrene. The ultra-violet absorption data of the hydrocarbon and of its intermediates are discussed.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry, Physical chemistry
• Date of Award: 1952
• Depositing User: Enlighten Team
• Unique ID: glathesis:1952-78919
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 28 Feb 2020 12:09
• Last Modified: 28 Feb 2020 12:09
• URI: https://theses.gla.ac.uk/id/eprint/78919