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

Abstract

Abstract 2,5-Diallylpyrrole 1 reacts with an excess of nBuLi in hexane/diethylether to give the N,C,Ctrilithio reagent 2. 7Li 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 H2O, D2O, MeI, Me3SiCl and Me3SnCl 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).