Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Synthesis and Electrophilic and Nucleophilic Substitution Reactions of 6-Chloro-1-azaazulan-2-ones and 2,6-Dichloro-1-azaazulenes
Takashi TodaShuichi SetoTetsuo Nozoe
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1968 Volume 41 Issue 9 Pages 2102-2111

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Abstract

6-Chlorol-azaazulan-2-ones and 2,6-dichloro-1-azaazulenes have been synthesized from 2-amino-5-chlorotropone. By the investigation of their electrophilic and nucleophilic substitution reactions, it is proved that the electrophilic substitutions take place at the C-3 positions of those compounds, and that the nucleophilic substitutions occur at the C-6 positions and then at the C-2 positions. The tautomerism of 6-amino-2-chloro-1-azaazulene derivatives is discussed.

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