22984-59-4Relevant articles and documents
An analysis of the factors contributing to the regioselectivity observed in the opening of oxiranes
Kayser, Margaret M.,Morand, Peter
, p. 302 - 306 (2007/10/02)
The regioselectivity of epoxide ring opening can be analyzed in terms of hard-soft acid base (HSAB) theory.The coordination of the hard acid with the oxigen atom of the oxirane ring produces a "pulling effect" which determines the direction of the ring opening.In the absence of strong "pulling effect" the "pushing effect" of the approaching base is examined and the consequences of relative softness or hardness of the nucleophile on the regioselectivity of the ring opening are discussed.