Reactions of alcohols in acetic anhydride-mineral acid mixtures
Degree GrantorUniversity of Canterbury
Degree NameDoctor of Philosophy
The reaction of 3β-cholestanol with acetic anhydride and sulphuric acid has been studied. A kinetic investigation has been made of the reaction of these reagents with cyclohexanol, 1-methylcyclohexanol and a series of benzyl alcohols. The relative rates for the reaction of some 6β-substituted-3β-acetoxycholestan-5α-ols in this system have been determined and the rates compared with that for 1-methylcyclohexanol. The reaction of 3β,6β-diacetoxycholestan-5α-ol with fluosulphonic acid has been shown to involve a "backbone" rearrangement terminated at a position intermediate between those usually found. The structure of one of the products has been determined and a structure is suggested for another product.