Reactions of epoxides of the pyran series involving ring expansion. Reaction of 4-methyl-3,4-epoxytetrahydropyran with potassium thiocyanate

The reaction of 4-methyl-3,4-epoxytetrahydropyran with potassium thiocyanate occurs with expansion of the oxirane ring and leads to 6-methyl-8-amino-3,7-dioxa-9-thiabicyclo4,3,0]nonane, the formation of which has been proven by the fact that products of its acylation by acid chlorides of 2-R-cinchonic acids are obtained, and also by the formation of Mannich bases when it is treated with formaldehyde and secondary amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1039–1042, August, 1992.