TV-methylpyrroles

Migration of the perfluoromethylthio group occurs in perfluoroalkyl acetylenic thiol esters and substituted TV-methylpyrroles [78, 79] (equation 18)... 

One of the earliest examples of the use of palladium in pyrrole chemistry was the Pd(OAc)2-induced oxidative couphng of TV-methylpyrrole with styrene to afford a mixture of olefins 26 and 27 in low yield based on palladium acetate [33]. 

N-alkylpyrroles are metallated much less easily than furan and thiophene. This is reflected in the higher temperature, longer reaction time and excess of the pyrrole derivative necessary to obtain a satisfactory yield in the subsequent alkylation (compare the metallation conditions with those in the preceding experiments). If no excess of A-methylpyrrole were used, THF would seriously compete with this substrate for butyllithium in the end stage of the metallation. In other experiments in this chapter (14, 39, 40) TV-methylpyrrole is metallated under different conditions, which permit a more economic use of this compound. 

Electrosynthesized polymers of TV-methylpyrrole (NMPy) and A -methylpyrrole-2,6-dimethyl-P-cyclodextrin (NMPy P-DMCD) were characterized with cyclic voltammetry and in situ conductivity measurements in aqueous and nonaqueous solutions [23]. In situ UV-vis-spectra of PNMPy and poly(NMPy-P-DMCD) films show differences both in band absorbances and in energies of polaronic transitions. SUght positive potential shifts are observed for poly(NMPy-P-DMCD) in aqueous and nonaqueous solutions compared to PNMPy films. This observation may be a result of the hydrophobic monomer NMPy, partly or entirely included in the CD s hydrophobic cavity. The results of in situ conductivity measurement for films in this investigation indicate that the resistivity of films that prepared in nonaqueous solution in acetonitrile + LiC104 are lower than resistivity of films prepared in LiC104 aqueous solution by approximately an order of magnitude. 

Addition reactions of 2-substituted N- methylpyrroles with C- acetyl-TV- phenylnitrilimine gave double cycloaddition products, spiro-cycloadducts and noncyclic bis-adducts (78JHC293). 

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