NBS or DEAD as effective reagents in α-thiocyanation of enolizable ketones with ammonium thiocyanate

Ketones possessing α-hydrogen undergo smooth thiocyanation with ammonium thiocyanate in the presence of N-bromosuccinimide (NBS) at room temperature in acetonitrile under neutral conditions to produce the corresponding α-ketothiocyanates in excellent yields with high selectivity. The use of NBS make...

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Bibliographic Details
Published in:Tetrahedron letters 2011-03, Vol.52 (13), p.1432-1435
Main Authors: Reddy, B.V. Subba, Reddy, S. Madhu Sudana, Madan, Ch
Format: Article
Language:English
Subjects:
Acetonitrile
Aliphatic compounds
Ammonium thiocyanate
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Ketones
N-Bromosccinimide
Organic chemistry
Preparations and properties
Selectivity
Tetrahedrons
Thiocyanates
α-Ketothiocyanates
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Summary:Ketones possessing α-hydrogen undergo smooth thiocyanation with ammonium thiocyanate in the presence of N-bromosuccinimide (NBS) at room temperature in acetonitrile under neutral conditions to produce the corresponding α-ketothiocyanates in excellent yields with high selectivity. The use of NBS makes this procedure simple, convenient and cost effective. In addition, diethyl azodicarboxylate (DEAD) was also found to promote this reaction under mild conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.01.035