Metal-free transfer hydrochlorination of internal C–C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chloride

Weidkamp, Andreas J.Oestreich, Martin2022-04-112022-04-112021-12-200022-4936https://depositonce.tu-berlin.de/handle/11303/16695http://dx.doi.org/10.14279/depositonce-15473The development and application of a transfer hydrochlorination reagent based on a trichlorinated bicyclo[3.1.0]hexane core that transfers two molecules of HCl per molecule of surrogate to a π-basic substrate under B(C6F5)3 catalysis is reported. Lewis acid-assisted chloride abstraction followed by thermal electrocyclic cyclopropyl-to-allyl cation ring opening releases ring strain as a previously unexploited driving force.en540 Chemie und zugeordnete WissenschaftenC–C triple bondshydrogen chloridehydrochlorinationtransfer hydrochlorination reagenttrichlorinated bicyclo[3.1.0]hexaneMetal-free transfer hydrochlorination of internal C–C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chlorideArticle1364-548X