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Synthesis of Acrylonitriles through an FeCl 3 ‐Catalyzed Domino Propargylic Substitution/Aza‐Meyer–Schuster Rearrangement Sequence
Author(s) -
Hao Lu,
Wu Feng,
Ding ZongCang,
Xu SuXia,
Ma YanLi,
Chen Li,
Zhan ZhuangPing
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200763
Subject(s) - domino , cyanation , substitution (logic) , sequence (biology) , catalysis , chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , computer science , organic chemistry , biochemistry , programming language
Nontoxic cyanide source : An unprecedented route to acrylonitriles by employing propargylic alcohols and para ‐tolylsulfonohydrazide as a combined cyano source has been developed (see scheme). This efficient and practical cyanation reaction proceeds through an FeCl 3 ‐catalyzed domino propargylic substitution/aza‐Meyer–Schuster rearrangement sequence, the rearrangement process of which is reported for the first time.