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Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides

Kwanghyun No1, Jeong Hyeon Lee, Seung Hwan Yang

  • 1Department of Chemistry, Sookmyung Women's University, Seoul 140-742, Korea.

The Journal of Organic Chemistry
|April 27, 2002
PubMed

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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