Dihydroxylation of styrene by sodium chlorite with scandium triflate. (3rd August 2016)

• Record Type: Journal Article
• Authors: Ohkubo, Kei; Hirose, Kensaku; Shibata, Takekatsu; Takamori, Kiyoto; Fukuzumi, Shunichi
• Is Part Of: Journal of physical organic chemistry. Volume 30:Number 5(2017)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2016-08-03
• Subjects: chlorine dioxide -- chlorite -- dihydroxylation -- electron paramagnetic resonance -- Lewis acid; Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3619
• Languages: English
• ISSNs: 0894-3230

Abstract

Abstract: Dihydroxylation of styrene by chlorite (ClO2 − ) with scandium triflate [Sc(OTf)3 ] occurs efficiently to produce 1‐phenylethane‐1, 2‐diol under the ambient conditions. Scandium triflate acting as a strong Lewis acid is found to accelerate thedisproportionation of ClO2 − to produce ClO − and ClO3 − . A scandium‐chlorine dioxide complex (Sc 3+ ClO2 ) is generated by the reaction of ClO − with ClO2 − in the presence of Sc 3 + . The binding of Sc 3 + to ClO2 was detected by the electron paramagnetic resonance measurements, enhancing the reactivity and selectivity of styrenehydroxylation . Abstract : The yield of dihydroxylated product was dramatically increased by addition of Sc 3 + . The Sc 3 + ClO2 complex is a reactive species for the dihydroxylation of styrene. ClO2 was efficiently generated by the reaction of NaClO2 with Sc 3 + .