Chiral pyrylium salts are almost unknown in the literature. We have applied the reaction of acyl chlorides with tert-butanol to the preparation of two new C2 symmetry pyrylium tetrafluoroborate salts, and acyl chlorides with dypnone to the preparation of two new C1 symmetry salts. We have obtained derivatives from the acid chlorides of 2-methyl-cyclohexanoic acid and 4-t-butyl-cyclohexanoic acid. These pyrylium salts form diastereomers upon epimerization and thus are amenable to study epimerization at alpha centers. The ease of epimerization a-pyrylium chiral centers has not been reported. The results of the kinetic studies and the comparison between the C1 and C2 symmetry will be discussed.

Kinetic studies of the epimerization of chiral centers alpha to a pyrylium salt ring

245th National Meeting (2013)

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