
TY  - JOUR
A1  - Banciu, MD 
A1  - Brown, RFC 
A1  - Coulston, KJ 
A1  - Eastwood, FW 
A1  - Jurss, C 
A1  - Mavropoulos, I 
A1  - Stanescu, M 
A1  - Wiersum, UE 
T1  - Formation of Cyclopent[<I>hi</I>]acephenanthrylene From 1,2-, 1,3-, 1,4- and 2,3-Triphenylenedicarboxylic Acid Derivatives on Flash Vacuum Pyrolysis at >900&#176;C
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 9
SP  - 965
EP  - 976
KW  - 
UR  - https://doi.org/10.1071/CH9960965 
N2  - The processes involved in the conversion of triphenylene , C18H12, into cyclopent [hi] acephenanthrylene, C18H10, under flash vacuum pyrolytic conditions at 900-1100&#176;C have been investigated by pyrolysing triphenylene-1,2- and -2,3-dicarboxylic anhydrides and diallyl triphenylene-1,3- and -1,4-dicarboxylates to give the corresponding didehydrotriphenylenes in the gas phase. These didehydro intermediates are converted into mixtures of cyclopent [hi] acephenanthrylene and triphenylene in different yields and proportions. Pyrolysis of 9,10-diethynylphenanthrene. C18H10, yields cyclopent [hi] acephenanthrylene in good yield. Pyrolysis of 1-nitrotriphenylene and allyl triphenylene-2-carboxylate to give the triphenylen-1-yl and -2-yl radicals leads to formation of the same products. Mechanisms involving radical rearrangements (C18H11 species) and benzyne-cyclopentadienylidenecarbene and ethyne-ethenylidene rearrangements (C18H10 species) are discussed. 
ER  -

