Research Output per year
Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to >50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.
- benzenoid compunds
- alkene syn dihydroxylation
Griffith, J. C., Jones, K. M., Picon, S., Rawling, M. J., Kariuki, B. M., Campbell, M., & Tomkinson, N. C. O. (2010). Alkene syn dihydroxylation with malonoyl peroxides. Journal of the American Chemical Society, 132(41), 14409-14411. https://doi.org/10.1021/ja1066674