The simplest epoxide, a three-membered ring. Opening by a carbon nucleophile, followed by protonation, adds a two-carbon primary-alcohol unit.
Nucleophilic cleavage of one epoxide C–O bond, with inversion at the attacked carbon under an SN2-like mechanism.
Concerted oxygen transfer from a peroxycarboxylic acid to an alkene. Hydrogen bonding to a nearby alcohol can influence reaction site and facial selectivity.
The epoxide across adjacent carbons of a cyclohexane ring. Backside nucleophilic opening produces an anti relationship between the introduced group and retained oxygen.
An unsymmetrical epoxide with two methyl substituents at one ring carbon. Acidic opening can favour nucleophile attachment to that more substituted carbon.
A 1,2-anhydro sugar derivative obtained by epoxidizing a glycal. Its anomeric carbon can undergo direct nucleophilic opening or ionization assisted by the ring oxygen.
Articles by others on the same topic
There are currently no matching articles.