Diaziridines carbenes from

By analogy with cyclopropane formation from carbenes and C=C bonds, azo compounds might be expected to give diaziridines in their reaction with carbenes. Although acyclic ADC compounds react readily with diazoalkanes... 

Three-membered rings with two heteroatoms are usually encountered only as reagents. Diazirines are nsefnl carbene precnrsors" - they are generally more stable than the equivalent isomeric diazo compounds, thongh they are sometimes explosive in the pure state. They can be prepared by oxidation of diaziridines that, in tnm, are available via the condensation of a ketone or aldehyde with ammonia and chloramine. Chloro-diazirines, from the reaction of amidines with hypochlorite, wiU undergo Sn2 or Sn2 displacement reactions."" ... 

These compounds are most often prepared as precursors for diazirines, which serve as a source of carbenes. Fluorodiaziridines made for this purpose are generally synthesized from oxime tosylates, as illustrated with that derived from a,a,a-trifluoro-3-methoxyacetophenone (236), which gives diaziridine 237 in 74% yield. Similarly,... 

Most of the work concerning the modification of carbene reactivity has been performed on cyclodextrins (CD) with reactive alkyl carbenes. Diazirines have proven to be the most convenient precursors due to the small size of the three-membered ring and the volatility of the leaving group, molecular nitrogen. Diazirines are usually obtained from the corresponding ketone in two steps in a methanolic solution of ammonia, hydroxylamine-0-sulfonic acid (HOSA) is added yielding a diaziridine which then is oxidized to the diazirine, most conveniently with iodine. 

---