Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, Croatia.
Beilstein J Org Chem. 2011 Mar 2;7:270-7. doi: 10.3762/bjoc.7.36.
N-(4-homoadamantyl)phthalimide (5) on excitation and population of the triplet excited state underwent intramolecular H-abstractions and gave products 6 and 7. The major product, exo-alcohol 6 was a result of the regioselective δ H-abstraction and the stereoselective cyclization of the 1,5-biradical. Minor products 7 were formed by photoinduced γ H-abstractions, followed by ring closure to azetidinols and ring enlargement to azepinediones. The observed selectivity to exo-alcohol 6 was explained by the conformation of 5 and the best orientation and the availability of the δ-H for the abstraction.
N-(4-同金刚烷基)邻苯二甲酰亚胺（5）在激发三重态激发态并使其分子内发生 H 提取，得到产物 6 和 7。主要产物，外消旋醇 6 是 1,5-双自由基区域选择性 δ H 提取和立体选择性环化的结果。次要产物 7 通过光诱导的 γ H 提取形成，随后环化生成氮杂环丁醇和扩环生成氮杂环庚二酮。通过 5 的构象和最佳取向以及 δ-H 的提取可用性，解释了对外消旋醇 6 的观察到的选择性。
