Density functional theory investigation of the deprotonation of oxete

The deprotonation of oxete by ether solvated methyl lithium was investigated by geometry optimization of reactants, transition states and products using the density functional theory (DFT) method (B3LYP/6-31++G(d,p)). The calculations suggest that allylic deprotonation is favored over the corresponding vinylic process by 1.5 kcal/mol in the transition structures and 1.7 kcal/mol in the products. This is in contrast to previous calculations of products (MP2/6-31++G(d,p)//HF/6-31++G(d,p)) that favored vinylic deprotonation.