Synthesis and spectra of aldehyde- and ketone-O-(2,5-dihydro-2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oximes — Thermal sources of some methoxy(oximino)carbenes

Abstract

Ten new oxadiazoline sources of methoxy(oximino)carbenes were synthesized by exchanging the acetoxy group of 2-acetoxy-2-methoxy-Δ3-1,3,4-oxadiazoline with an oximino group. The new compounds were characterized by means of spectroscopy and the formation of carbenes upon thermolysis of a few was demonstrated by means of interception with tert-butyl alcohol. The carbenes fragmented to form methoxycarbonyl and iminyl radicals.Key words: 2,2-dioxyoxadiazoline, methoxy(oximino)carbene, oxadiazole, radical pair, rearrangement.