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Title: A study of the rearrangement products from isoxazolopyridinium salts
Author: Phipps, John R.
Awarding Body: Keele University
Current Institution: Keele University
Date of Award: 1973
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Brief treatment of tetrahydro-4-oxoisoxazolo [2,3-a] pyridinium bromide and its 3-methyl derivative with boiling acetic anhydride gave 4-acetyl-5,6-dihydro-4H-furo [3,2-b] pyrid-2-one and its 3-methyl counterpart. The structures of these rearrangement products have been proved by complete hydrogenation, spectroscopy and X-ray diffraction studies. The 2-methylisoxazolo [ 2,3-a ] pyridinium salt did not undergo the rearrangement; this suggests a keten or an isoxazoline intermediate. When 4,5,6,7-tetrahydro-4-hydroximinoisoxazolo [2,3-a] pyridin1um bromide or chloride were heated with acetic anhydride, rearrangement to 4-acetyl-7-halogeno-5,6-dihydro-4H-pyrrolo [3,2-b] pyrid-2-one occurred. Mechanisms for the rearrangement have been suggested. Photolysis of the rearrangement products led to the isolation of dimers. Photolysis of 5,6-dihydro-4H-furo [3,2-b] pyrid-2-one gave a dimer when using benzene as the solvent; when methanol was used 4-hydroxy-3-methoxymethylamino-hexa-2,4-dienoic acid lactone was produced.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry