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  • Facile synthesis of beta-tribromomethyl and dibromomethylenated nitroalkanes via conjugate addition of bromoform to nitroalkenes.

Facile synthesis of beta-tribromomethyl and dibromomethylenated nitroalkanes via conjugate addition of bromoform to nitroalkenes.

The Journal of organic chemistry (2009-02-26)
Bichismita Sahu, Guddeangadi N Gururaja, Shaikh M Mobin, Irishi N N Namboothiri
ABSTRACT

Addition of bromoform to conjugated nitroalkenes in the presence of Mg provided beta-tribromomethyl nitroalkanes in good to excellent yields and diastereoselectivity. These novel Michael adducts, formed under radical conditions, underwent elimination of HBr in the same pot under reflux to afford beta-dibromomethylenated nitroalkanes in good yield. Alternatively, a one-pot high yielding synthesis of the dibromides was possible under anionic conditions via LDA mediated addition of bromoform to nitroalkenes.

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Supelco
Bromoform solution, certified reference material, 5000 μg/mL in methanol
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Bromoform, contains 60-120 ppm 2-methyl-2-butene as stabilizer, 99%
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Bromoform, amylene stabilized, analytical standard
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Sigma-Aldrich
Bromoform, contains 1-3% ethanol as stabilizer, 96%
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