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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 7, Number 4
April 20, 1986 

Chemistry of the 3a,7a-Dihydro-1H-indole Esters. Aromatization by Bromine
Chang Kiu Lee*, Yu Mi Ahn, In-Sook Han Lee
A series of tetramethyl 1-substituted benzyl-3a,7a-dihydro-1H-indole-2,3,3a,4-tetracarbo xylates were prepared and their reactions with bromine were examined. The initial reaction seemed to be the formation of the intermediate N-bromo quaternary ammonium bromide. This intermediate underwent aromatization with loss of the 3a-methoxycarbonyl group. Bromine replaced the N-substituent of the p-methoxybenzyl compound and addition of bromine occurred across the C6-C7 double bond of the indole ring. Bromination of the benzyl ring and aromatization occurred for the m-methoxybenzyl compound.
311 - 314
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