Phosphorus reagents are used in synthetic chemistry labs around the world on a daily basis. Indeed, most undergraduate chemists are familiar with the Wittig, Mitsunobu and Appel reactions. Despite being very useful these reactions they all have one big drawback, namely, the generation of phosphine oxides as stoichiometric waste products. This means that the reactions cannot be easily used on a large scale as they generate huge amounts of waste that has to be separated from the product.
Dr Ross Denton and his group are trying to solve the phosphine oxide problem by developing phosphine oxide-catalysed versions of these reactions - turning the waste product product into the catalyst for the reactions. The work described in a recent Chem Comm paper is the first example of catalytic chlorination of alcohols under Appel conditions. Here triphenylphosphine oxide, the waste product formed in the classical version of the reaction, is used as a catalyst for the chlorination reaction. The result is a mild catalytic chlorination reaction that is 90 % more efficient.
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