%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 (3ad), where the X substituents can be transformed to hydrogen-bond donor groups to afford new CTV-based heteroditopic receptors. The substituents of compounds 3ad 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