Premium
On the ‘livingness’ of a dynamic library of cyclophane formaldehyde acetals incorporating calix[4]arene subunits
Author(s) -
Cacciapagliaa Roberta,
Di Stefanoa Stefano,
Mandolinia Luigi
Publication year - 2008
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1357
Subject(s) - chemistry , cyclophane , carbocation , formaldehyde , alkoxy group , monomer , ether , stereochemistry , polymer chemistry , photochemistry , molecule , organic chemistry , alkyl , polymer
The acid catalyzed transacetalation of cyclophane formaldehyde acetals incorporating calix[4]arene subunits generates a short‐lived dynamic library of macrocycles. The side reaction responsible for the loss of ‘livingness’ is the unexpected decomposition of monomeric units into a bridged ether and formaldehyde. A plausible mechanism is suggested, in which the crucial step is the formation of benzyl carbocations strongly stabilized by the alkoxy substituents at the lower rim of the calix[4]arene moieties. Copyright © 2008 John Wiley & Sons, Ltd.