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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.

MATERIALS
Product Number
Brand
Product Description

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