Li Jing, Okuda Yasuhiro, Zhao Jiaji, Mori Seiji, Nishihara Yasushi
Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushimanaka, Okayama 700-8530, Japan.
Org Lett. 2014 Oct 3;16(19):5220-3. doi: 10.1021/ol5026519. Epub 2014 Sep 24.
An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate α-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.
已开发出一种将氰基取代的亚氨基异苯并呋喃直接转化为其相应的烷基2-氰基苯甲酸酯的有效方法。这种转化通过起始亚氨基异苯并呋喃中C-C、C-O和C-N键的断裂进行。密度泛函理论（DFT）研究表明，中间体α-亚氨基腈是通过2-亚氨基苯甲酸酯与氰离子之间形成C-C键原位生成的。DFT计算中以更热力学的方式生成异氰化物作为副产物也支持了实验结果。
