Organic Chemistry (2009)

Alken-1-yl Triphenylphosphonium Salts are known to be moderately reactive Michael acceptors and dienophiles or dipolarophiles in Diels-Alder or 1,3-dipolar cycloaddition reactions respectively. The project will deal with investigation of reaction sequences comprising the nucleophilic addition or cycloaddition to the alken-1-yl triphenylphosphonium salts followed by Wittig reaction of the intermediately generated triphenylphosphonium ylides. The requisite alken-1-yl triphenylphosphonium salts will be prepared by reaction of alken-1-yl nonaflates with triphenylphosphine catalyzed by tetrakis(triphenylphosphine)palladium(0).