ChemInform Abstract: Structures and Tropicity of Hydrogenation Products of a Bisdehydro[13]annulenone and a Bisdehydro[15]annulenone.

✍ Scribed by H. HIGUCHI; N. HIRAIWA; T. DAIMON; S. KONDO; J. OJIMA; M. IYODA; G. YAMAMOTO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199816083

✦ Synopsis

Structures and Tropicity of Hydrogenation Products of a Bisdehydro [13]annulenone and a Bisdehydro [15]annulenone.

-Catalytic partial hydrogenation of bisdehydro[13]annulenone (I) affords two isomeric dehydro[13]annulenones (II) and (III) and [13]annulenone (IV), representing the first example of a monocyclic non-dehydro annulenone derivative larger than tropone. (IV) is found to be atropic on the basis of 1 H NMR spectra. Molecular mechanics studies indicate the non-planarity of the skeleton and therefore a lack of peripheral conjugation. In contrast to these results, bisdehydro[15]annulenone (V) can not be converted to the corresponding [15]annulenone by the described hydrogenation method.