(1) New Methods of Approach to the Bicyclo[5:3:0]decane System. (2) Attempted Synthesis of the Indacenes

Islam, Ahmad M (1954) (1) New Methods of Approach to the Bicyclo[5:3:0]decane System. (2) Attempted Synthesis of the Indacenes. PhD thesis, University of Glasgow.

Abstract

PART I. NEW METHODS OP APPROACH TO THE BICYCLO[5:3:0]DECANE SYSTEM. A. Condensation of propargyl bromide with 2-ethoxy-carbonylcycloalkanones furnishes products which, by hydration and subsequent ring closure, give bicyclic compounds with a five-membered ring fused to the ring of the starting material. e. g. Condensation of cycloheptanone with readily available acetylenic Mannich bases gives products which may be converted directly to bicyclo [5:3:0] decane derivatives by heating with formic acid-phosphoric acid e.g. C. Substituted cyclohexanones are subjected to ring expansion with a diazo-compound of such a nature that the resulting cycloheptanone possesses a side chain capable of condensing with the ring carbonyl group to yield bicyolo[5:3:0]decane derivatives directly. PART II. ATTEMPTED SYNTHESIS OP THE INDACENES. Attempted syntheses of the postulated quasi-aromatic hydrocarbons, symmetrical and assymmetrical indacenes have been investigated which involve dehydrogenation of the relevant hydroindacenes. The structure assigned to a supposed derivative of s-indacene reported in the literature has been shown to be erroneous.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1954
• Depositing User: Enlighten Team
• Unique ID: glathesis:1954-79122
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 31 Mar 2020 09:09
• Last Modified: 31 Mar 2020 09:09
• URI: https://theses.gla.ac.uk/id/eprint/79122