The first spontaneous resolution of a sulfoxide: Dianin's compound analogue, (R)-4-(4-hy-droxy-phen-yl)-2,2,4-tri-methyl-thia-chroman-1-oxide.

ABSTRACT: The title sulfoxide, C₁₈H₂₀O₂S, was prepared by controlled oxidation of thia-Dianin's compound using hydrogen peroxide in glacial acetic acid. On recrystallization from glacial acetic acid, it was found to form unsolvated, spontaneously resolved crystals, the initial crystal structure analysis revealing the presence of both sulfoxide epimers in the crystal. On multiple recrystallization a single epimer was observed, with crystallization occurring in the unchanged ortho-rhom-bic space group P2₁2₁2₁, with Z' = 1. The mol-ecule possesses a distal conformation, referring to the juxtaposition of the p-hydoxyphenyl substituent with respect to its syn-related methyl group, with the sulfoxid

SUBMITTER: Gall JH 

PROVIDER: S-EPMC6218920 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature