Synthesis of Triptycene and Pentiptycene Halides via Nucleophilic Aromatic Substitution of Triflate Precursors
Journal
Journal of the Chinese Chemical Society
Journal Volume
59
Journal Issue
3
Pages
399-406
Date Issued
2012
Author(s)
Abstract
Abstract An efficient synthesis of a series of new pre‐functionalized triptycene and pentiptycene building blocks is reported. The key reaction is the nucleophilic aromatic substitution (S N Ar) of the cyano‐substituted iptycene triflates with halide salts to afford the corresponding iptycene halides. Among the various halide salts investigated, LiI and LiBr provide the best yield of the S N Ar products, namely, cyano‐substituted iptycene iodide and bromide, respectively. Despite the different iptycene scaffold, the triptycene and pentiptycene substrates display similar S N Ar reactivities under the reaction conditions.
Type
journal article