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DOI: 10.1039/A608584I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1457-1464

Reactions involving fluoride ion. Part 42.1 Heterocyclic compounds from perfluoro-3,4-dimethylhexa-2,4-diene

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Richard D. Chambers, William K. Gray, Steven J. Mullins and Stewart R. Korn

Abstract

Reactions of perfluoro-3,4-dimethylhexa-2,4-diene 1 with primary aromatic amines give both pyrrole 2 and pyrroloquinoline 3 derivatives, whilst ammonia gives dienes 10 and 12 as well as the novel pyrrole derivative 11. Catechol leads to a benzodioxocine system 18 and this can be epoxidised to a mixture of mono- 21 and di-epoxides 20. Electrocyclisation of 18 occurs with ultraviolet irradiation, giving 22.

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