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Perfluoroglutaric acid when treated with methyl magnesium iodide afforded
hexafluoro-2,6-dimethylpyran-2,6-diol in high yield and 2,213,3,4,4-hexafluoro-
5-oxocaproic acid in low yield. The former appeared to exist in a range
melting form (61.-79°C) and also in a very labile form melting at 96-98°C.
Problems associated with the formation of this latter form were investigated.
The hexafluoro-2,6-dimethylpyran-2,6-diol yielded a monosemi-carbazone and
also a mono and a di1(2,4-dinitrophenylhydrazone). The mono (2,4-dinitro
phenylhydrazone) appeared to be cyclic. Reduction, both with lithium aluminium
hydride and sodium borohydride yielded 3,3,4,415,5-hexafluoro-n-heptane-2,6-diol.
Reaction with anhydrous calcium sulphate gave 3,3,414,515-hexafluoro-2-
methylcyclohex-l-ene-6-one.
The acid product of the original reaction of perfluoroglutaric acid and
methyl magnesium iodide was characterised as a 2,4-dinitrophenylhydrazone and
as an S-benzylthiouronium salt. Infra-red spectroscopic evidence suggests
the latter compound exists in a straight chain form. |
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