
TY  - JOUR
A1  - Anderson, MR 
A1  - Brown, RFC 
A1  - Coulston, KJ 
A1  - Eastwood, FW 
A1  - Ward, A 
T1  - The Pyrolysis of Phenylnaphthalenedicarboxylic Anhydrides: Products of Ring Contraction and of Radical Cyclization
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1990
VL  - 43
IS  - 7
SP  - 1137
EP  - 1150
KW  - 
UR  - https://doi.org/10.1071/CH9901137 
N2  - Naphthalene-1,2,-dicarboxylic anhydrides with neighbouring phenyl substituents give on flash vacuum pyrolysis (850-900&#176;/0.02-0.04 mm) ring-contracted carbenes which insert into the phenyl groups. The 8- phenyl anhydride (7) gives acephenanthrylene (10) as the major product, and the 3-phenyl anhydride (15) gives 1,2 : 4,5-dibenzopentalene (indeno [2,1-a]indene) (18). The anhydrides (7) and (15) were   synthesized by pyrolysis of the corresponding 1-naphthylmethyl propynoates (2) and (13) through a new one-step process of intramolecular Diels -Alder addition/retro-Diels -Alder elimination of acetylene. 1-Phenylnaphthalene-2,3-dicarboxylic anhydride (19) on pyrolysis at 960&#176;/0.02 mm gives fluoranthene (11) as the major product. The behaviour of the 1-C6D5 compound (24) suggests involvement of a radical cyclization process. 
ER  -

