An ether with oxygen directly attached to an alkene carbon. Electrophilic activation and hydrolysis can convert an appropriate enol ether back to a carbonyl compound.
An alcohol protecting group that is often stable to strong bases and organometallic reagents but can be removed under mild acid conditions.
An ether with oxygen directly attached to a vinylic carbon, in the simplest terminal example. oxygen resonance donation strongly differentiates the two alkene carbon shifts.
A silyl ether contains an O–Si bond, commonly protecting an alcohol or phenol. Cleavage at electrophilic silicon releases an oxygen-centered anion under suitable conditions.
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.
, an ether formed by trapping a triphenylmethyl carbocation with ethanol, followed by deprotonation.
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