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Abstract
The optically active arylethylmethyloxosulfonium perchlorates (2a-c) were prepared by the oxidation of the corresponding sulfonium salts (la-c) with sodium perbenzoate. The absolute configurations of oxosulfonium salts were determined by converting them into aryl ethyl sulfoxides (3a-c). From the relationship of the absolute configurations of ethylmethylphenylsulfonium perchlorate (1a) and ethylmethylphenyloxosulfonium perchlorate (2a), it was found that the oxidation of sulfonium salt (+)-(S)-1a with sodium perbenzoate proceeded with retention of configuration around the sulfur atom to afford oxosulfonium salt (+)-(R)-2a. The circular dichroism (CD) spectra of optically active oxosulfonium perchlorates (2) with (+)-(R) configuration show a positive strong Cotton effect at ca. 230nm and a positive weak one at ca. 260nm. Whereas, the CD spectra of optically active oxosulfonium perchlorates (2) with (-)-(S) configuration show a negative strong Cotton effect at ca. 230 nm and a negative one at ca. 260 nm.