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.
On the ' livingness ' of a dynamic library of cyclophane formaldehyde acetals incorporating calix[4]arene subunits / Cacciapaglia, R; DI STEFANO, Stefano; Mandolini, Luigi. - In: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY. - ISSN 0894-3230. - STAMPA. - 21:(2008), pp. 688-693. [10.1002/poc.1357]
On the ' livingness ' of a dynamic library of cyclophane formaldehyde acetals incorporating calix[4]arene subunits
DI STEFANO, Stefano;MANDOLINI, Luigi
2008
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
