Pi Bonds Increase Reactivity When Breaking an Alkyl Ester Bond

Abstract

Methyl acetate and vinyl acetate were used to analyze the breaking of the less reactive alkyl carbon-oxygen bond in an ester functional group. The alkyl carbon, bonded to the non-carbonyl oxygen of both esters, was replaced with a bond to a platinum complex, (dippe)Pt(NBE)2. With varied time and temperature conditions of each reaction, both esters reacted to form the desired product in good yield. Vinyl acetate, containing an alkene functional group, and therefore, a pi bond on the alkyl carbon substituent, proved to react at less harsh conditions and was found to form a more stable complex when bound to the platinum. DFT computed transition states for each possible product were compared with free reactants to assist with analyzing vinyl acetate forming the more favorable product based on activation energy. Exploring the reactivity of two different esters provides the further understanding into electron donation and attraction, hard and soft atoms and their properties, pi bonds and their influence on the reactivity of a molecule, and the potential of different syntheses with esters.