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

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.