2-Acetoxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline and acetoxy(methoxy)carbene

Article abstract of DOI:10.1139/v03-126

2-Acetoxy-2-methoxy-5,5-dimethyl-Δ³-1,3,4-oxadiazoline undergoes two competitive 1,3-dipolar cycloreversions at 110°C. It loses N₂, presumably to afford a short-lived carbonyl ylide that fragments to acetone and acetoxy(methoxy)carbene. It also forms 2-diazopropane and the appropriate mixed anhydride. It is the only currently known source of acetoxy(methoxy)carbene.