Synthesis of 1-haloethenamides from ynamide through halotrimethylsilane-mediated hydrohalogenation.

Authors :: Ohashi, Kazuhiro
Mihara, Shigenori
Sato, Akihiro H.
Ide, Masataka
Iwasawa, Tetsuo
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Jan2014, Vol. 55 Issue 3, p632-635. 4p.
Publication Year :: 2014
Abstract: Abstract: A convenient synthesis of 1-haloethenamides has been achieved by utilizing halotrimethylsilane (TMSX, X=Cl, Br, I) and water. Halotrimethylsilane in 1M CH2Cl2 solution functions as a halogen source of the in situ generated HX, and the HX added to the terminal triple bonds of ynamides in Markovnikov fashion. [Copyright &y& Elsevier]

Subjects :: *AMIDE synthesis
*YNAMIDES
*METHYLSILANE
*HALOGENATION
*TRIPLE bonds (Chemistry)
*SOLUTION (Chemistry)

Language :: English
ISSN :: 00404039
Volume :: 55
Issue :: 3
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 93584172
Full Text :: https://doi.org/10.1016/j.tetlet.2013.11.091

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