%0 Journal Article
%A Arduini, Arturo
%A Calzavacca, Francesco
%A Demuru, Domenico
%A Pochini, Andrea
%A Secchi, Andrea
%D 2004
%T Synthesis of Cavity Extended
Cyclotriveratrylenes
%U https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Cavity_Extended_Cyclotriveratrylenes/3349333
%R 10.1021/jo035557m.s001
%2 https://acs.figshare.com/ndownloader/files/5188645
%K cyclotriguaiacylene 1
%K COCH 3
%K Cavity Extended Cyclotriveratrylenes Aromatic nucleophilic substitution reaction
%K alkylation reactions
%K stereoisomeric mixture
%K CTV derivatives
%K fluorobenzene derivatives
%K compounds 3
%K CN
%K CHO
%K para position
%K unsymmetrical compounds
%K X substituents
%K demethylation reaction
%K 8 c
%K cyclotriveratrylene derivatives
%X Aromatic nucleophilic substitution reaction of
cyclotriguaiacylene 1 with fluorobenzene derivatives bearing
electron-withdrawing groups X (CHO, COCH3, CN, NO2) in
the para position gives a series of cyclotriveratrylene derivatives (3a−d), where the X substituents can be transformed
to hydrogen-bond donor groups to afford new CTV-based
heteroditopic receptors. The substituents of compounds
3a−d favor the facile demethylation reaction of the CTV
derivatives. Attempts to perform alkylation reactions on
derivatives (8c,d) evidenced the formation of a stereoisomeric mixture of symmetrical and unsymmetrical compounds.
%I ACS Publications