Rapid Photoracemization of Chiral Alkyl Aryl Sulfoxides.

ABSTRACT: The photoracemization of chiral alkyl aryl sulfoxides with a photosensitizer has not been sufficiently investigated thus far. Therefore, in this study, a rapid photoracemization reaction of enantiopure alkyl aryl sulfoxides using 1 mol % 2,4,6-triphenylpyrylium tetrafluoroborate (TPT⁺) was developed. Various substitution patterns were tolerated and every racemization reaction proceeded extremely fast (k₂ = 1.77 × 10⁴-6.08 × 10¹ M^-1 s^-1, t_1/2 = 0.4-114 s). Some chiral sulfoxides with easily oxidizable functional groups are not appropriate for this photoisomerization. The electrochemical potentials of the functional groups, determined via cyclic voltammetry, are useful for predicting the reactive or no

SUBMITTER: Makino K 

PROVIDER: S-EPMC8650104 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature