Probing the Peroxycarbenium [3+2] Cycloaddition Reactions with 1,2‐Disubstituted Ethylenes: Results and Insights

• Published in: Chemistry : a European journal Vol. 23; no. 9; pp. 2031 - 2034
• Main Authors: Xu, Ze‐Jun, Wittlin, Sergio, Wu, Yikang
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 10.02.2017; Wiley Subscription Services, Inc
• Subjects: Alkenes; Bonding; Carbon; Chemical bonds; Chemistry; Chemistry, Multidisciplinary; Cycloaddition; Oxygen; Oxygen atoms; peroxides; Physical Sciences; rearrangement; ring expansion; Science & Technology; Terminals; ORGANIC PEROXIDES; cycloaddition; SINGLE; ring expansion; C BOND FORMATION; MALARIA; ANTIMALARIAL PEROXIDES; alkenes; peroxides; 1,2-DIOXOLANES; rearrangement

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 bo...