ol5026519_si_001.pdf (1.51 MB)
Skeletal Rearrangement of Cyano-Substituted Iminoisobenzofurans into Alkyl 2‑Cyanobenzoates Catalyzed by B(C6F5)3
journal contribution
posted on 2014-10-03, 00:00 authored by Jing Li, Yasuhiro Okuda, Jiaji Zhao, Seiji Mori, Yasushi NishiharaAn
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.