par Fuks, Robert ;Viehe, Heinz Günter
Référence Bulletin des Sociétés chimiques belges, 86, 3, page (219-235)
Publication Publié, 1977
Article révisé par les pairs
Résumé : When ynamines 1 react with electrophiles R⊕; X ⊕, the structure of the products depends strongly on the nature of the electrophilic reagent and of the ynamine. The protonation under various conditions leads only to the cyclobutenylcyanine (D) whereas the methylation and the bromination give either (D) and/or the allenamidinium salt (F). Steric factors in the presumed intermediate enaminoketenimium salt (C) appear to decide on the course of the reaction. The keteniminium, existing in equilibrium with its α‐haloenamine tautomeric form (A ⇌ B), is most probably the initial adduct of 1 and RX. Copyright © 1977 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim