Please login first
x Selected file doesn't exist!
Unexpected Tosyl Migration in Acid Catalyzed Dehydration of 4-hydroxy-4-methyl-5-tosyl-2-cyaniminohexahydropyrimidines
* ,
1  Department of Organic Chemistry, M.V.Lomonosov State Academy of Fine Chemical Technology, 119571 Moscow, Russian Federation

Abstract: Base-catalyzed dehydration of 2-cyanimino-4-hydroxy-4-methyl-5-tosylhexahydropyrimidines gives expected 2-cyanimino-5-tosyl-1,2,3,4-tetrahydropyrimidines. However, acid-catalyzed dehydration leads to mixture of the latter compounds and the products of tosyl group migration, namely 2-cyanimino-4-tosylmethyl-1,2,3,4-tetrahydropyrimidines. Plausible explanation of the obtained data is proposed.
Keywords: N-cyanoguanidine; N-cyano-N'-(1-tosyl-1-alkyl)guanidines; tosylacetone; 2-cyanimino-4-hydroxy-5-tosylhexahydropyrimidines; dehydration; 2-cyanimino-5-tosyl-1,2,3,4-tetrahydropyrimidines; 2-cyanimino-4-tosylmethyl-1,2,3,4-tetrahydropyrimidines; tosyl migration

 
 
Top