
%0 Journal Article
%A Dachriyanus, 
%A Sargent, Melvyn V. 
%A Skelton, Brian W. 
%A White, Allan H. 
%T Cycloadducts of Benzynes and 3,4-Dimethoxyfuran.
%J Australian Journal of Chemistry
%D 2000/07/21
%V 53
%N 4
%P 267-275
%K Adduct; benzyne; dimethoxyfuran; methoxy-substituted benzynes; X-ray structure.
%R https://doi.org/10.1071/CH99116
%U https://www.publish.csiro.au/paper/CH99116 
%X Cycloaddition between benzyne and 3,4-dimethoxyfuran (1) yielded 2,3-dimethoxy-1,4-dihydro-1,4- epoxynaphthalene (3) which was unusually labile. On chromatography and exposure to air, it yielded (1&#945;,3&#946;,4&#945;)-3-methoxy-3,4-dihydro-1,4-epoxynaphthalen-2(1H)-one (4) and (5&#945;,5a&#946;,6a&#945;,7&#946;,12&#946;,12a&#945;,13a&#946;,14&#945;)-6a,12a,13a-tri-methoxy-6a,7,12,12a,13a,14-hexahydro-5,14:7,12-diepoxydinaphtho&#91;2,3-b:2&#8242;,3&#8242;-e&#93;&#91;1,4&#93;dioxin-5a(5H)-ol (19). A single-crystal X-ray structure determination was performed on compound (19). The chemistry of the ketone (4) was investigated. Cycloadditions were also carried out with 3,4-dimethoxyfuran (1) and methoxy-substituted benzynes. The regiochemistry of hydrolysis of the resultant adducts was explored. 
