The chemical and physical properties of aromatic compounds are reviewed. Particular reference is made to the nuclear magnetic resonance interpretation of aromaticity,and several examples of its application are presented. An attempt is made to estimate the aromaticity of the five membered rings of indole,benzofuran and benzothiophene by means of nuclear magnetic resonance spectroscopy. The described method of calculation gives the aromaticity of these rings as 4496,30% and 61%, respectively,of that of benzene. The nuclear magnetic resonance spectra of the monomethylindenes,monomethylindoles,monomethylbenzo-furans and monomethylbenxothiophenes show that there is a small coupling (J-1c./sec) between the 3— and 7-proton: The cyclisation of beta-(m-toly1)-propionic acid and m-cresoxyacetyl chloride has been studied and both cyclisations have been found to yield a mixture of products. Each of these mixtures has been separated to give two ketones. Two of these ketones (7-methylindan-1-one and 4-methylcoumaran-3-one) have not been described previously. The unambiguous preparation of 4-,5-,6-and 7-methylindene is described.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:602197 |
| Date | January 1963 |
| Creators | Foster, Richard Gregory |
| Contributors | Jackman, L. M. ; Elvidge, J.A |
| Publisher | Imperial College London |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/10044/1/13250 |
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