
%0 Journal Article
%A McAlpine, JB 
%A Riggs, NV 
%T Nitration and bromination reactions of galbulin
%J Australian Journal of Chemistry
%D 1975/04/01
%V 28
%N 4
%P 831-847
%K 
%R https://doi.org/10.1071/CH9750831
%U https://www.publish.csiro.au/paper/CH9750831 
%X Nitration of the 1-phenyltetralin lignan, galbulin, occurs initially with dealkylative nitration at C 9 and cleavage of the C 1-C 9 bond. Subsequent reaction of the carbonium ion formed at C 1 with nitrate ion, and the degree of nitration of the aromatic rings, determine the final products. In contrast, bromination is not dealkylative and occurs initially at C 6? in ring c and subsequently at C 5 (ring A). Bromination in acetic acid in the presence of pyridine is accompanied by an unusual aromatic reaction, acetoxylation at C 8. 
