title: Probing the Peroxycarbenium [3+2] Cycloaddition Reactions with 1,2-Disubstituted Ethylenes: Results and Insights.
abstract: The causes for the title reaction to be limited to only the alkenes with an unsubstituted terminal alkenic carbon were explored. In some "failed" cases the cycloaddition products actually formed but rearranged concurrently. An oxygen atom or a N-Boc (Boc=tert-butyloxycarbonyl) group at the double bond was proven essential for acquisition of intact [3+2] cycloaddition products from 1,2-disubstituted ethylenes.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Ze-Jun
authors.initials: ZJ
authors.lastname: Xu
authors.affiliation: Swiss Tropic and Public Health Institute, Socinstrasse 57, 4002, Basel, Switzerland.|University of Basel, 4051, Basel, Switzerland.
authors.forename: Sergio
authors.initials: S
authors.lastname: Wittlin
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Yikang
authors.identifier: http://orcid.org/0000-0003-4501-5401
authors.initials: Y
authors.lastname: Wu
keywords: alkenes; cycloaddition; peroxides; rearrangement; ring expansion