Use this URL to cite or link to this record in EThOS: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.735269
Title: Studies in the aromatic hydrocarbons
Author: Gorrie, James R.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1964
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Abstract:
At face value the evidence from the above synthesis appears almost conclusive. However, on further study of Nenitzescu's publication (3), it seems probable that the cyclodehydration of the tertiary alcohol (XVII) does not give a homogeneous product. Further support for this view comes from the work of Evans and Smith (11) who have reported the disproportionation of a tetrahydro-10,11-benzfluoranthene (XIX) in the presence of polyphosphoric acid. They treated a -tetralone at 1700 with polyphosphoric acid and isolated 10,11- benzfluoranthene and the hydrocarbon of Dansi and Ferri (A) as products. The ketone ( XVIII) originally produced reacts in its enol form to give a tetrahydro -10,11 -benzfluoranthene (XIX), which then disproportionates into the octahydro10,11- benzfluoranthene (A), and 10,11- benzfluoranthene (II). From the results of this work, the possibility of disproportionation during Nenitzescu's cyclodehydration reaction cannot be ruled out entirely. One further factor which Nenitzescu did not consider concerns the stereochemistry of the hydrogen atoms at positions 9 and 14 in the molecule. Each of the substances A and B should be capable of existing in two forms depending on the configuration of these two hydrogen atoms. Since Nenitzescu's synthesis involves the interaction of two reduced naphthalene moieties, it would neither preclude the formation of nor engender a particular configuration of these hydrogen atoms. Further study of the structure of A therefore appeared worthwhile, and an unambiguous synthesis of A by classical organic techniques is described in the sequel. This synthesis also provides information about the configuration of the hydrogen atoms 011 carbon atoms 9 and 14.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.735269  DOI: Not available
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