Synthesis of Medium-Sized-Ring Compounds

Jhaveri, Dinbala Bhagilal (1960) Synthesis of Medium-Sized-Ring Compounds. PhD thesis, University of Glasgow.

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Part One: The work discussed in this part of the thesis was undertaken with a view to synthesising hydroxy-tropones by the ring expansion of the six-membered ring. The acid-catalysed rearrangements of the opoxides of methyleneanthrone , benzylideneanthrone, and 2-benzylidene-1-tetralone have been studied and attempts have been made to rearrange the dibromides of methyleneanthrone and 2-benzylidene-1-tetralone by means of silver oxide. None of these compounds but the opoxide of 2-benzylidene-1-tetralone smoothly rearranged by acid or boronrifluoride etherate to a seven-membered ring. 4:5-Dihydroxy-2:3-6:7-dibenzecycleheptadien-1-one first prepared by Treibs and Klinkhammer was rigorously shown to have the cis-configuration. The trans-isomer was also prepared, and the solubility of the two diols in alkali was explained by postulating a hemi-ketal structure and it is clearly not due to an o-quinonoid structure as suggested by Treibs and Klinkhammer. Part Two: As a model for a proposed synthesis of caryophyllene, the preparation of 1-carbothoxy-5-methylbicycle (3,3,1) non-3-ene-9-one and its attempted conversion to 5-methylseyele3oct-4-ene-1:5-dicarboxylic acid has been examined. The structure and mode of origin of two rearrangement products encountered in this work have been investigated and in the light of these results, the synthesis of 1-carbothoxy-5-methylbicycle (3,2,1) oct-6-ene-8-one has been undertaken. The successful synthesis of this compound is discussed in terms of a model synthesis of longifolene.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1960
Depositing User: Enlighten Team
Unique ID: glathesis:1960-79392
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 31 Mar 2020 09:09
Last Modified: 31 Mar 2020 09:09

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