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Org Lett. 2010 Jan 15;12(2):332-5. doi: 10.1021/ol902667a.

Structure-reactivity relationships: reactions of a 5-substituted aziadamantane in a resorcin[4]arene-based cavitand.

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Institute of Organic Chemistry, University of Vienna, Wahringer Strasse 38, A-1090 Vienna, Austria.


The complexation properties of two novel C5-substituted adamantanediazirines within the resorcin[4]arene-based cavitand 4 were investigated in DMSO-d(6), revealing that binding is up to 1.4 kcal/mol stronger for halogenated adamantanediazirines when compared with the unsubstituted species. The thermal behavior of 5-bromo-2-aziadamantane (3) was investigated by DSC analysis as the first representative of the adamantanediazirine family in the neat solid state, as well as encapsulated within the aromatic cavity of cavitand 4. In the solid phase, the reactions of photolytically or thermolytically generated 5-bromo-2-adamantanylidene (11) can be controlled by complexation within cavitand 4.

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