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The Aza Curtius Rearrangement
Author(s) -
Yagupolskii Lev M.,
Shelyazhenko Svetlana V.,
Maletina Irina I.,
Petrik Vitalij N.,
Rusanov Eduard B.,
Chernega Alexander N.
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200104)2001:7<1225::aid-ejoc1225>3.0.co;2-6
Subject(s) - curtius rearrangement , chemistry , sodium azide , acetonitrile , medicinal chemistry , yield (engineering) , azide , guanidine , organic chemistry , metallurgy , materials science
On interaction of N ‐(trifluoromethylsulfonyl)carboximidoyl chlorides (analogs of acyl chlorides in which the carbonyl oxygen atom is substituted by the more strongly electron‐withdrawing =NSO 2 CF 3 group) with sodium azide in glyme or acetonitrile at −5 to +10 °C, dinitrogen is eliminated quantitatively and carbodiimides RN=C=NSO 2 CF 3 are formed in high yield. In other words, an aza Curtius rearrangement occurs. The carbodiimides react with water, alcohols, and secondary amines to give corresponding ureas, isoureas, and guanidine derivatives. Imidoyl chlorides with substituents other than SO 2 R F do not enter into the aza Curtius reaction.