期刊
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
卷 21, 期 7-8, 页码 688-693出版社
JOHN WILEY & SONS LTD
DOI: 10.1002/poc.1357
关键词
dynamic covalent chemistry; dynamic combinatorial chemistry; transacetalation; reaction mechanism; cyclodepolymerization; metathesis; ring-ring equilibrium
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 (c) 2008 John Wiley & Sons, Ltd.
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