Skatole dimer, structure

Again based on the failure of 2-methylindole to form a dimer, Schmitz-DuMont proposed structure (29) for skatole dimer. Structure (30) was, however, shown to be the correct one independently in three... 

The structure (39) proposed for this compound by analogy with indole and skatole dimers was confirmed by an analysis of the NMR spectrum. ... 

The dimerization of skatole proceeds in an entirely analogous manner, cation (44) now being the electrophilic reagent. This is sufficiently reactive to effect substitution at the a-position of a neutral skatole molecule. Attack by the less hindered side of cation (44) will be favored, leading to the stereochemistry shown in structure (30). The failure of 2-methylindole to dimerize is paralleled by the failure of 2-methylpyrrole dimer to react with a further molecule of 2-methylpyrrole. The main reason is almost certainly again the reduction in the electrophilic character of the immonium carbon by... 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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