Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of a-Pinene

The development of several unique strategies and tactics for the synthesis of a-pinene isotopologues that has culminated in access to all eight possible isomers with deuterium incorporated selectively at each available carbon atom is described. Access to this library of isotopologues provides new tools to more fully investigate the atmospheric autoxidation of a-pinene, a complex process that plays a major role in the formation of secondary organic aerosol (SOA) in the Earth’s atmosphere.