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2,5-Diallylpyrrole 1 reacts with an excess of  n BuLi in hexane/diethylether to give the N,C,Ctrilithio reagent 2.  7 Li NMR spectra of 2 in THF/ HMPTA at low temperature indicate the presence of an ionic species. Reactions of 2 in THF with electrophiles such as H 2 O, D 2 O, MeI, Me 3 SiCl and Me 3 SnCl lead selectively to the cisisomers 3a - 6a, whereas the analogous reactions in hexane or diethylether afford mixtures containing both cis- and rram-isomers (e.g. 3b).

Notizen: Synthesis of N,C,C-Trilithio-2,5-diallyl-pyrrole and its Solvent-Controlled Reactions with Electrophiles Notizen