Diaziridines

Diaziridines
Diaziridine

Diaziridines are heterocyclic organic chemical substances that contain a three-membered ring consisting of two nitrogen atoms and one carbon atom, with the two nitrogen atoms forming an azine group (–NN–). The diaziridines belong to the larger group of three-ring compounds with two heteroatoms in the ring.

properties

Some diaziridines are neurotrophic .

synthesis

A carbonyl reacts with ammonia or a primary amine and an amination reagent such as hydroxylamine- O- sulfonic acid (HOSA) under basic conditions. The aminal is then closed .

Reactivity

The oxidation of 3,3-dimethyl-diaziridine leads to 3,3-dimethyl-diazirine:

Unsubstituted diaziridines can also be oxidized with I ₂ / NEt ₃ to form the more stable diazirines . Diaziridines react with electrophilic groups such as ketenes or isocyanates with ring enlargement.

Individual evidence

↑ Synthesis of monocyclic diaziridines and their fused derivatives; NN Makhova, VY Petukhova, VV Kuznetsov, Arkivoc , 2008 (i), 128–152 ( PDF ).
^ ^A ^b Siegfried Hauptmann : Organic Chemistry , 2. Revised edition, VEB Deutscher Verlag für Grundstoffindindustrie, Leipzig, 1985, ISBN 3-342-00280-8 , p. 561.

[1] Synthesis of monocyclic diaziridines and their fused derivatives; NN Makhova, VY Petukhova, VV Kuznetsov, Arkivoc , 2008 (i), 128–152 ( PDF ).

[Hauptmann1-2] A ^b Siegfried Hauptmann : Organic Chemistry , 2. Revised edition, VEB Deutscher Verlag für Grundstoffindindustrie, Leipzig, 1985, ISBN 3-342-00280-8 , p. 561.