Novel Synthetic Chemistry of Ureas and Amides

1. Front Matter

   Pages i-xvii

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2. Introduction

   • Marc Hutchby

   Pages 1-35

3. Pd(II) Catalysed Aminocarbonylation of Alkenes

   • Marc Hutchby

   Pages 37-44

4. Carbonylation of Aryl Ureas

   • Marc Hutchby

   Pages 45-55

5. Urea Hydrolysis

   • Marc Hutchby

   Pages 57-70

6. Amide Hydrolysis

   • Marc Hutchby

   Pages 71-88

7. Conclusions and Future Work

   • Marc Hutchby

   Pages 89-94

8. Experimental

   • Marc Hutchby

   Pages 95-160

9. Back Matter

   Pages 161-166

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In this thesis, the author investigates the chemistry and application of molecules containing urea and amide bonds. These bonds are some of the strongest known and are fundamental to biological processes. The author describes his discovery that sterically hindered ureas undergo solvolysis at room temperature under neutral conditions. This is a remarkable finding, since ureas are inert under these conditions and a general rule of chemistry is that hindered substrates are less reactive. Remarkably, the author translates these results to the correspondingly sterically hindered amides. This thesis has resulted in a number of outstanding publications in high profile journals. The unique method for breaking urea and amide bonds developed in this study is likely to have far reaching consequences for biological protein manipulation.

• Amide Hydrolysis
• C-H Activation
• Mild Solvolysis
• Neutral Solvolysis
• Palladium Catalysed Carbonylation
• Rapid Solvolysis
• Urea Hydrolysis

• , Thomas Graham House, Royal Society of Chemistry, Cambridge, United Kingdom

  Marc Hutchby

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