Reversible Friedel-Crafts Acylations of Phenanthrene: Rearrangements of Acetylphenanthrenes

Author(s): Liron Levy, Sergey Pogodin, Shmuel Cohen, Israel Agranat.

Journal Name: Letters in Organic Chemistry

Volume 4 , Issue 5 , 2007

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Abstract:

The study of Friedel-Crafts acetylation of phenanthrene with acetic acid in polyphosphoric acid, along with rearrangements and deacetylations of acetylphenanthrene isomers, indicated its reversibility. The structures of (E)-2- AcPHN and (Z)-9-AcPHN were determined by X-ray crystallography. PM3 calculations predicted that 9-AcPHN is the kinetically controlled while 2-AcPHN and 3-AcPHN are the thermodynamically controlled products, in accordance with experiment. The mutual rearrangements of 2-AcPHN and 9-AcPHN are noted.

Keywords: PPA, overcrowding, Agranat-Gore rearrangement, deacylation, PM3 calculations, X-ray crystallography

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Article Details

VOLUME: 4
ISSUE: 5
Year: 2007
Page: [314 - 318]
Pages: 5
DOI: 10.2174/157017807781212120
Price: $58

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