Keten. Part 19. The reactions of 2,4,6-trimethylbenzonitrile N-oxide with ketens

Abstract

Diphenylketen, t-butylcyanoketen, and dimethylketen react with the title nitrile oxide to form 1:1 adducts shown to have the oxazolinone structures (5); keten, t-butylethoxycarbonylketen, and phenyl isocyanate fail to react. The nitrile oxide is deoxygenated by diphenylketen and dimethylketen; in the latter case a new type of deoxygenation process occurs forming the unsaturated ketone (11) and thence the isoxazoline (8).