Synthesis of Acrylonitriles through an FeCl3-Catalyzed Domino Propargylic Substitution/Aza-Meyer-Schuster Rearrangement Sequence

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 FeCl3‐catalyzed domino propargylic substi...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-05, Vol.18 (21), p.6453-6456
Main Authors: Hao, Lu, Wu, Feng, Ding, Zong-Cang, Xu, Su-Xia, Ma, Yan-Li, Chen, Li, Zhan, Zhuang-Ping
Format: Article
Language:English
Subjects:
Acrylonitrile - chemical synthesis
Acrylonitrile - chemistry
acrylonitriles
Aza Compounds - chemistry
Catalysis
Chemistry
Chlorides - chemistry
cyanides
domino reactions
Ferric Compounds - chemistry
Fluoroquinolones - chemistry
iron
Molecular Structure
Naphthyridines - chemistry
propargylic substitution
rearrangement
Trimethylsilyl Compounds - chemistry
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Summary: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 FeCl3‐catalyzed domino propargylic substitution/aza‐Meyer–Schuster rearrangement sequence, the rearrangement process of which is reported for the first time.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201200763