Talk:Pictet–Spengler reaction
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Mechanism
[edit]Would it not be somewhat simpler to proceed through the following path?
Pgpotvin (talk) 20:09, 2 August 2016 (UTC)
- I've often seen the rearrangment mechanism in textbooks (initial reaction at C3 of the indole), and is in keeping with the usual Indole#Electrophilic substitution pattern. Maybe better to base an analysis on things like Baldwin's rules, which agrees with your mechanism (direct reaction at C2 of the indole) and is how the German Wikipedia article (de:Pictet-Spengler-Reaktion) explains it, rather than just what seems simple. To the library! Chem. Rev. article by Cox an Cook (1995) cited as ref#15 seems to have pretty good evidence for each way depending on substrate details. Feel free to update our article to include the other reaction pathway. DMacks (talk) 20:41, 2 August 2016 (UTC)