Abstract
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.
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