Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Chemistry of the 3a,7a-Dihydro-1H-indole Esters. Aromatization by Bromine$^\dag$

  • Lee, Chang-Kiu (Department of Chemistry, Kangweon National University) ;
  • Ahn, Yu-Mi (Department of Chemistry, Kangweon National University) ;
  • Han Lee, In-Sook (Department of Science Education, Kangweon National University)
  • Published : 1986.08.20
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Abstract

A series of tetramethyl 1-substituted benzyl-3a,7a-dihydro-1H-indole-2,3,3a,4-tetracarboxylates 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 $C_6-C_7$ double bond of the indole ring. Bromination of the benzyl ring and aromatization occurred for the m-methoxybenzyl compound.

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References

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