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Three‐Membered Rings Containing Two Hetero‐Atoms
Author(s) -
Schmitz Ernst
Publication year - 1964
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196403331
Subject(s) - chemistry , dehydrogenation , ring (chemistry) , oxidizing agent , diazo , diimide , thermal decomposition , reagent , computational chemistry , stereochemistry , combinatorial chemistry , molecule , organic chemistry , perylene , catalysis
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 NN double bond without destruction of the three‐membered ring. Thermal decomposition yields carbenes.