Institute of Organic Chemistry, University of Vienna, Wahringer Strasse 38, A-1090 Vienna, Austria.
Org Lett. 2010 Jan 15;12(2):332-5. doi: 10.1021/ol902667a.
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.
研究了两种新型 C5-取代金刚烷二氮杂环丁烷在基于间苯二酚[4]芳烃的主体 4 中的络合性质，在 DMSO-d(6)中，与未取代的物种相比，卤素取代的金刚烷二氮杂环丁烷的结合能高达 1.4 千卡/摩尔。通过 DSC 分析研究了 5-溴-2-氮杂金刚烷（3）的热行为，作为金刚烷二氮杂环丁烷家族的第一个代表，在纯固态以及主体 4 的芳香空腔内被包合。在固态下，光解或热解生成的 5-溴-2-金刚烷亚基（11）的反应可以通过主体 4 内的络合来控制。
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