Reactions of 4-(Diethylamino)selenet-2(2H)-imine with Nucleophiles – Synthesis of 2-Methylen-3-oxobutane Selenoamides

Author(s): Plamen K. Atanassov, Anthony Linden, Heinz Heimgartner

Journal Name: Letters in Organic Chemistry

Volume 7 , Issue 4 , 2010

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3-Acetyl-N-(4-bromophenyl)-4-(diethylamino)selenet-2(2H)-imine (5a), which is conveniently obtained from the formal [2+2] cycloaddition of 4-bromophenyl isoselenocyanate and 4-(diethylamino)-3-butyn-2-one, reacts with amines, alcohols, water, and thiophenol to give the corresponding 2-methylen-3-oxobutane selenoamides 7 in good yields via ring opening to the ketenimine 6 and subsequent addition of the nucleophile.

Keywords: Ketenimines, ring opening, selenet-2(2H)-imines, selenium heterocycles, selenoamides, X-ray crystallography

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Article Details

Year: 2010
Published on: 01 March, 2012
Page: [291 - 297]
Pages: 7
DOI: 10.2174/157017810791130685
Price: $65

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