Skatole dimer with 2-methylindole

Methylindole is, however, incorporated into mixed dimers and trimers. It thus reacts with indole and with skatole to form mixed dimers, and 2 moles react with 1 mole of indole for form a mixed trimcr. Likewise indole forms a dimer with 1,2-dimethylindole, 2-phenylindole, and even with 2,5-dimethylpyrrole, ... 

Skatole (3-methylindole) readily forms a dimer hydrochloride with HCl in ether or with 15% aqueous HCl, as docs 1,3-dimethyl-indole. 3-n-Propylindole is also readily dimerized in dry ether/HCl/ ... 

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 -- [ , , ]

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