
%0 Journal Article
%A Blair, IA 
%A Mander, LN 
%A Mundill, PHC 
%T Studies on intramolecular alkylation. XIII. The synthesis of 3,4-Dihydrophenanthren-2(1H)-ones from Pummerer intermediates
%J Australian Journal of Chemistry
%D 1981/06/01
%V 34
%N 6
%P 1235-1242
%K 
%R https://doi.org/10.1071/CH9811235
%U https://www.publish.csiro.au/paper/CH9811235 
%X 1-Methylsulfinyl-4-(naphthalen-1'-yl)butan-2-ones (12)-(15) were rearranged and cyclized to the 1-methylthio-3,4-dihydrophenanthren- 2(1H)-ones (17)-(20), respectively, by trifluoroacetic anhydride. Hydrogenolysis of (18)-(20) furnished the parent ketones (9), (25) and (26). Evidence is provided to show the involvement of an Ar1-5 route in the formation of (18) and (19), including the formation of spiro ketone (23) from sulfoxides (14) and (16). Acid catalysed cyclization of diazoketone (5) gave either phenanthren-3-one (8) or spiro ketone (10) depending on the conditions employed. 
