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]
Scheda prodotto non validato
Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo
Titolo: | On the ' livingness ' of a dynamic library of cyclophane formaldehyde acetals incorporating calix[4]arene subunits | |
Autori: | ||
Data di pubblicazione: | 2008 | |
Rivista: | ||
Citazione: | 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] | |
Handle: | http://hdl.handle.net/11573/226903 | |
Appartiene alla tipologia: | 01a Articolo in rivista |