title: Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3.
abstract: 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.
authors.affiliation: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushimanaka, Okayama 700-8530, Japan.
authors.forename: Jing
authors.initials: J
authors.lastname: Li
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Okuda
authors.forename: Jiaji
authors.initials: J
authors.lastname: Zhao
authors.forename: Seiji
authors.initials: S
authors.lastname: Mori
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Nishihara
mesh_terms: D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D001572:Benzofurans / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics; D005466:Fluorocarbons
chemical_list: D001565:Benzoates; D001572:Benzofurans; D001880:Boranes; D006845:Hydrocarbons, Fluorinated; D009570:Nitriles; C547049:tris(pentafluorophenyl)borane; D005466:Fluorocarbons