
%0 Journal Article
%A Ridley, DD 
%A Smal, MA 
%T Preparations of 6-substituted 6H-Dibenzo[b,d]thiopyrans and their S-oxides through nucleophilic additions to 6H-dibenzo[b,d]thiopyran-6-one
%J Australian Journal of Chemistry
%D 1983/04/01
%V 36
%N 4
%P 795-802
%K 
%R https://doi.org/10.1071/CH9830795
%U https://www.publish.csiro.au/paper/CH9830795 
%X Methods for the preparations of 6-substituted 6H-dibenzo[b,d]thiopyrans and the corresponding S-oxides were explored. The most general procedure involved the addition of Grignard reagents to 6H-dibenzo[b,d]thiopyran-6-one, whereupon 6-substituted 6H-dibenzo[b,d]thiopyran-6-ols were formed. The carbonyl group in the thioester thus behaved like an isolated ketone in its reactions with nucleophiles. The resultant dibenzothiopyran-6-ols were acid-labile, and dehydration products underwent further modification in some instances. Oxidation of the olefins afforded stable S-oxides. The dianion formed by reduction of dibenzothiophen also offered routes to 6-substituted 6Hdibenzo[b,d]thiopyrans, but the reactions of this dianion were non-regioselective and thus were of limited use. 
