55368-39-3Relevant academic research and scientific papers
Electrosynthesis of arylpyrroles and -indoles under S(RN)1 conditions
Chahma,Combellas,Thiebault
, p. 366 - 368 (1994)
Arylpyrroles and -indoles are electrosynthesized via a S(RN)1 type reaction. With pyrrolyl anion, the reaction leads mainly to α-substitution, but β-substitution and disubstitution are also observed. With indolyl anion, the main product corresponds to β-substitution. In both cases, the yield of the main product is higher than 50%.
Delocalized Nitrogen Carbanions in SRN1 Reactions
Chahma, M.,Combellas, C.,Thiebault, A.
, p. 8015 - 8022 (2007/10/03)
SRN1 reactions can be performed with nitrogen carbanions as nucleophiles, and generally the reaction leads to a mixture of isomers.In the case of the pyrrolyl anion, position 2 is about four times more reactive than position 3.When the ortho positions of pyrrole are substituted by alkyl groups, the reactivity of position 2 increases while that of position 3 decreases.With tert-butyl groups as the substituents, no reaction at position 2 is observed.With the indolyl anion as the nucleophile, no substitution at position 2 or at the phenyl ring is observed, and only one product corresponding to monosubstitution at position 3 is obtained.Imidazolyl anions react preferentially at position 4 (5), and substitution of position 2 by a methyl group makes the coupling regioselective.
