
%0 Journal Article
%A Halton, Brian 
%A Evans, David A. C. 
%A Warrener, Ronald N. 
%T Studies in the Cycloproparene Series: Approaches to Cyclopropa[<emph type="2">b</emph>]tetracenes
%J Australian Journal of Chemistry
%D 2000/03/14
%V 52
%N 12
%P 1123-1126
%K 
%R https://doi.org/10.1071/CH99136
%U https://www.publish.csiro.au/paper/CH99136 
%X Cyclopropa&#91;b&#93;naphthalene-3,6-dione (2) fails to add furan across the enedione olefinic bond in a Diels&#8211;Alder cycloaddition even at 14 &#215; 105 kPa. In contrast, isobenzofuran (4) adds efficiently at ambient temperature and pressure. The epoxytetracenedione (5) that is formed is air-sensitive and decomposes under conditions employed for dehydration. Aromatization of (5) to cyclopropatetracenedione (6) is not observed despite anthracene-1,4-dione (8) being obtained from its analogous tetrahydro precursor (7) under the same conditions. 
