Reactivity of enol carbonates with ozone

Several dienes of varying steric bulk containing an enol carbonate have bee n synthesized and reacted selectively with ozone at the isolated double bon ds. Rate measurements have been made for ozonolysis in a series of substitu ted cyclohexenes to demonstrate the unusually slow reactivity of the enol c arbonate. Proton and carbon NMR chemical shifts have been presented to show that the enol carbonate is not particularly electron deficient in its doub le bond. Calculation of partial charges from the Mulliken population analys is shows good correlation with the NMR data. The results suggest a carbonat e association with atone that slows the rate of carbon-carbon bond cleavage .