The Journal of Organic Chemistry

Reactions of oximes with thianthrene cation radical in nitrile solvents. Cycloaddition to form oxadiazoles and deoxygenation to form nitriles

S Chiou, A Hoque, HJ Shine

Index: Chiou, Shishue; Hoque, A. K. M. M.; Shine, Henry J. Journal of Organic Chemistry, 1990 , vol. 55, # 10 p. 3227 - 3232

Full Text: HTML

Citation Number: 16

Abstract

5-R-3-methyl-1, 2, 4-oxadiazole (3) was obtained from some reactions, that is, 3c alone from IC, and a mixture of 29 and 3a from la. Neither 2 nor 3 was obtained in measurable amounts from reactions of lg and lh. The aldehyde (RCHO) was obtained in small yields from each reaction. Thianthrene (Th) and thianthrene 5-oxide (Tho) were also major products. Studies with [180]-lb and ['80]-ld showed that the oxygen atom in 2 came entirely and in Tho ...