TY - JOUR
T1 - Reversible friedel-crafts acylations of phenanthrene
T2 - Rearrangements of acetylphenanthrenes
AU - Levy, Liron
AU - Pogodin, Sergey
AU - Cohen, Shmuel
AU - Agranat, Israel
PY - 2007/7
Y1 - 2007/7
N2 - The study of Friedel-Crafts acetylation of phenanthrente with acetic acid in polyphosphoric acid, along with re-arrangements 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.
AB - The study of Friedel-Crafts acetylation of phenanthrente with acetic acid in polyphosphoric acid, along with re-arrangements 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.
KW - Agranat-Gore rearrangement
KW - Deacylation
KW - Overcrowding
KW - PM3 calculations
KW - PPA
KW - X-ray crystallography
UR - http://www.scopus.com/inward/record.url?scp=36148990636&partnerID=8YFLogxK
U2 - 10.2174/157017807781212120
DO - 10.2174/157017807781212120
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AN - SCOPUS:36148990636
SN - 1570-1786
VL - 4
SP - 314
EP - 318
JO - Letters in Organic Chemistry
JF - Letters in Organic Chemistry
IS - 5
ER -