Solvent effect on regioselectivity of epoxide ring opening in styrene oxide by O- and N-nucleophiles in neutral and basic media

The results of ring opening in styrene oxide by alcohols, amines, amino alcohols, and diamines were generalized. On low polarizing ability of the solvent, the main direction of the process is the formation of normal α-substituted products. The solvent effect on regioselectivity of the reaction was studied for N,N-diethylethylenediamine. The ratio of products correlates well with the value of dielectric constant for mixed aqueous-organic solvents and with the parameters of polarity E _T and AN for neat solvents.