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A new reaction of N-bromoacetamide: facile addition to α-nitroalkenes

✍ Scribed by Werner Rank; Hans H. Baer

Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
269 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

Recently we have described2 the use of _N-bromoacetamide (NBA) as an efficient agent for a-bromination of secondary nitroalkane groupings in carbohydrates. The brominations were performed in aqueous methanol solution in the presence of sodium acetate. In connection with these studies the question arose in what way NBA would react with nitroalkenes. We now report that, in acetone or aqueous acetone solution and in the presence of a catalytic amount of sodium acetate, NBA adds itself smoothly at room temperature and in the dark across the olefinic bond to give B-acetamido-a-bromo-a-nitroalkanes. If the nitro group is situated in a terminal position, the a-hydrogen atom is replaced by another bromine atom and p-acetamido-a, a-dibromo-3 a-nitro derivatives are obtained. Thus, (3-nitrostyrene gave, in 65 % yield, 2-acetamido-1. ldibromo-l-nitro-2-phenylethane as colorless crystale from ethanol-water, m. p. 129-130°(dec.),

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