
%0 Journal Article
%A Johnson, DW 
%A Mander, LN 
%T Studies on intramolecular alkylation. X. The acid-catalysed reactions of 5,8-Dialkoxy-1,2,3,4-tetrahydronaphthyl diazomethyl ketones
%J Australian Journal of Chemistry
%D 1978/07/01
%V 31
%N 7
%P 1561-1568
%K 
%R https://doi.org/10.1071/CH9781561
%U https://www.publish.csiro.au/paper/CH9781561 
%X 5,8-Dimethoxy-3,4-dihydronaphthalen-1(2H)-one was converted into diazomethyl 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthyl ketone (10) which, when treated with trifluoroacetic acid at 0&#176;, gave 5,8- dimethoxy-4,4a-dihydro-3,4a-ethanonaphthalen-2(3H)-one (13), but at -15&#176; gave 8-methoxy-1,2,3,4-tetrahydro-3,4a-ethanonaphthalene- 5(4aH),10-dione (14). 6-Methoxy-3,4-dihydronaphtha-len-1(2H)-one reacted with m-chloroperoxybenzoic acid to give 4,5-dihydro-1-benzoxepin-2(3H)-one (15) which after hydrolysis, ethylation and polyphosphoric acid treatment gave 5-ethoxy-8-methoxy-3,4-dihydronaphthalen-1(2H)-one (17). This compound was transformed into 5-ethoxy-8-hydroxy-1,2,3,4-tetrahydro-2-naphthoic acid (19) and thence to the ethoxy analogue of (14). 
