PREPARATION AND ISOMERIZATION OF DICHLOROAMINO-3,5-DIFLUORORO-4- HEPTAFLUOROISOPROPYL-6-METHOXY PYRIDINE

Abstract
Treatment of 4-heptafluoroisopropyl-2-methoxy-3,5,6-trifluropyridine (4 )
with aqueous ammonia in THF gave 2-amino-3,5-difluoro-4-heptafluoroisopropyl-
6-methoxy pyridine (5) in 7 1% yield. Chlorination of this amine with
'ButOCl at -16°C gave an unstable product, namely 2-dichloroarnino-3,5-
difluoro-4-heptafluoroisopropyl-6-methoxy pyridine (6). Iodine-catalysed
rearrangement of this dichloroamino-compound provided a ca. 70:30 mixture of
3-chloro-6-chloroimino-3,5-difluoro- 4-heptafluoroisopropyl-2-methox y -I
azacyclohexa- l,4-diene (7) and 5-chloro-6-chloroirnino-3,5-difluoro-4-hepta fluoroisopropyl-
2-methoxy- 1 -azacyclohexa- l,3-diene(8). The C NMR spectra
of these imines have also been studied