Sustainability and Organic Chemistry

These objectives have spurred research directed toward developing alternative synthetic methods. Take alcohol oxidation, for example. As described in Section 15.9, primary alcohols are converted to aldehydes by oxidation with pyridinium chlorochromate (PCC). 

While this oxidation proceeds in synthetically satisfactory yield, it is inefficient in terms of atom economy. PCC is used in stoichiometric amounts and none of its atoms are incorporated into the desired product. Moreover, the toxicity of chromium compounds introduces significant hazardus-waste disposal problems. 

TEMPO-catalyzed oxidations are replacing more familiar oxidation methods, especially in the pharmaceutical industry. An early step in the synthesis of an HIV protease inhibitor is the oxidation shown where the desired ketone is formed in 98% yield in the presence of 1 mol % of TEMPO. 

The 4-hydroxy derivative of TEMPO is used as the catalyst for the synthesis of a key aldehyde intermediate in the large-scale preparation of progesterone and corticosteroids. 

Not only is the reaction itseif green, but the raw materiai for the synthesis is a piant steroi obtained from soybean waste. 

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Boxed essays- Fullerenes, Nanotubes, and Graphene updates the ever-expanding role of elemental carbon in its many forms in Chapter 11. Sustainability and Organic Chemistry is a new boxed essay in Chapter 15 that uses real-world examples to illustrate principles of green chemistry. 

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