411242-58-5Relevant articles and documents
Chromium-Templated Synthesis of Densely Substituted Distorted Arenes - Intramolecular Benzannulation of [(Alkynylaryl)alkenyl]carbene Complexes to Planar-Chiral Hydroquinoid [2.2]Heterametacyclophanes
Doetz, K. H.,Mittenzwey, S.
, p. 39 - 48 (2007/10/03)
{[(meta-Alkynylphenyl)alkenyl]carbene}chromium compounds 1 and 2 have been synthesized by four-step (or five-step) and seven-step sequences, starting from 3-halophenol or 3-haloaniline, respectively. This approach, involving high-yielding Takai reactions and lithium cuprate additions, provides a novel and straightforward route to [(alkynylaryl)alkenyl](methoxy)carbene complexes. Upon gentle warming in tetrahydrofuran, (carbene)chromium compounds of this type undergo intramolecular benzannulation to give novel [2.2]heterametacyclophanes 21 and 22, bearing two chiral planes arising from the unsymmetrical substitution patterns both of the cyclophane skeleton and of the newly formed, Cr(CO)3-coordinated benzohydroquinone deck.