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The Journal of organic chemistry

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


PMID 19239256

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.