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SPISSHAK
(Hive Bee) 06-21-02 08:18 No 323583 |
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dialkyltryptamine synthesis through alkyliodides. | Bookmark | |||||
I read shulgin`s book TIHKAL and notice when he alkylates typtamine with ethyl bromide. And eliminates alkylbromides from the quarternary ammonium halides with diazabicyclooctanes. Why doesn`t the indole nitrogen get alkylated??? Call me stupid about tryptamine chemistry I don`t care... |
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Lilienthal (Moderator) 06-21-02 16:09 No 323648 |
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indole nitrogen is not an amine | Bookmark | |||||
Because the indole nitrogen is not a normal amine. The nitrogen lone electron pair is donated to the aromatic ring system. Protonate or alkylate it and you destroy aromaticity - energetically very unfavorable.... |
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SPISSHAK (Hive Bee) 06-21-02 22:29 No 323744 |
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Thanks lillenthal | Bookmark | |||||
That answers my question thanks for the insight. |
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