Micellar Mediated Halodecarboxylation of α,β-Unsaturated Aliphatic and Aromatic Carboxylic Acids-A Novel Green Hunsdiecker-Borodin Reaction

A Novel Hunsdiecker-Borodin reaction (HBR) has been carried out efficiently with α,β-unsaturated aliphatic and aromatic carboxylic acids by using N-halo succinimides such as N-chloro succinimide (NCS), N-bromo succinimide (NBS), and N-iodo succinimide (NIS) under micellar media. The reaction with α,...

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Bibliographic Details
Published in:Journal of dispersion science and technology 2007-04, Vol.28 (4), p.613-616
Main Authors: Rajanna, K. C., Reddy, N. Maasi, Reddy, M. Rajender, Saiprakash, P. K.
Format: Article
Language:English
Subjects:
Chemistry
Colloidal state and disperse state
Exact sciences and technology
General and physical chemistry
halo decarboxylation
hunsdiecker-borodin reaction
Micelles
Micelles. Thin films
α, β-Unsaturated carboxylic acids
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Summary:A Novel Hunsdiecker-Borodin reaction (HBR) has been carried out efficiently with α,β-unsaturated aliphatic and aromatic carboxylic acids by using N-halo succinimides such as N-chloro succinimide (NCS), N-bromo succinimide (NBS), and N-iodo succinimide (NIS) under micellar media. The reaction with α,β-unsaturated aromatic carboxylic acids afforded β-halo styrenes in excellent yield while α,β-unsaturated aliphatic carboxylic acids underwent decarboxylation and to give corresponding halo derivatives. The reactions are dramatically accelerated in micellar media. This procedure works efficiently in CTAB (cetyl trimethyl ammonium bromide), SDS (sodium dodecyl sulfate), and TX (Triton-X-100) media under stirred conditions at room temperature. At reflux temperatures the yield of reaction products were further enhanced from good to excellent.
ISSN:0193-2691
1532-2351
DOI:10.1080/01932690701282690