Aziridine

Aziridine is a three-membered saturated ring containing one nitrogen atom and two carbon atoms. The name also denotes the parent compound C₂H₅N, whose strained ring makes it reactive.

Ring strain: Destabilization caused when molecular geometry forces bond angles away from their preferred values. Aziridine’s compressed ring angles contribute to its elevated reactivity.
Heterocycle: A cyclic compound whose ring contains at least one atom other than carbon. Aziridine is a compact nitrogen-containing member of this broad structural family.
Aziridine synthesis: Methods for preparing aziridines from alkenes, imines, or other nitrogen-containing precursors. Synthetic routes determine how substitution and stereochemistry are introduced into aziridine rings.
Epoxide: A three-membered cyclic ether containing one oxygen atom and two carbon atoms. Epoxides are oxygen analogues that undergo related, but not identical, ring-opening reactions.
Nucleophilic substitution: A reaction in which a nucleophile replaces a leaving group at an electrophilic atom. Nucleophiles can open activated aziridine rings by attacking a ring carbon.
Saturated compound: A compound whose carbon framework contains no carbon–carbon double or triple bonds. Aziridine’s ring has single bonds and is saturated.
Aziridination: The formation of an aziridine ring, commonly by transferring nitrogen to an alkene. Aziridination provides direct access to strained nitrogen heterocycles from alkenes.
Azetidine: A saturated four-membered ring containing one nitrogen atom and three carbon atoms. Adding one ring atom reduces angle strain relative to aziridine.
Electrophilic addition: A reaction in which an electrophile adds across a multiple bond or otherwise initiates bond formation. Electrophilic activation of aziridine nitrogen can promote nucleophilic ring opening.
Amine: An organic derivative of ammonia in which one or more hydrogen atoms are replaced by carbon groups. Aziridine’s ring nitrogen has amine-like bonding and basicity.

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