ISSN:
0570-0833
Keywords:
Strained molecules
;
Heterocycles
;
Diaziridines
;
Diazirines
;
Oxaziranes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Since their discovery five years ago, the diaziridines have become an extensive and easily accessible class of compounds. Hydrolysis of these compounds effects a simple synthesis of hydrazine, alkylhydrazines, and N,N′-dialkylhydrazines. They are also powerful oxidizing agents. The rigidity of the three-membered ring gives rise to a few stereoelectronic peculiarities. Investigations on the mechanism of formation of the three-membered rings led to a new synthesis of oxaziranes and to discovery of the isomeric oximes with a three-membered ring structure. The latter decompose readily to form diimide. Diazirines are cyclic isomers of the aliphatic diazo compounds and are surprisingly easy to obtain by dehydrogenation of suitable diaziridines; they are chemically much more stable than the linear isomers. Grignard reagents add onto the N=N double bond without destruction of the three-membered ring. Thermal decomposition yields carbenes.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.196403331
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