What is it about?
The classical bromination mechanism indicates the formation of bromonium ion as intermediate of the reaction delivering products in a stereospecific way, some substrates may lead to the mechanism via carbocation or may still have competition between the two types of mechanism. In this work, the addition of bromine to a dienamide produced erythro and threo diastereoisomers that were identified by NMR and theoretical calculations.
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Why is it important?
Bromination reactions are among the most important reactions in organic synthesis and can be carried out using bromine or many other bromine donor compounds, such as N-bromosuccinimide (NBS), bromonitromethane, cyanogen bromide, N-bromobenza- mide, carbon tetrabromide]. The electrophilic bromination of an alkene is considered a quintessential reaction of the double bond and is prortrayed in undergraduate textbooks as being a well understood process. The identification of the two products (via bromonium and carbocation) was performed by comparing the experimental and calculated NMR chemical shifts.
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This page is a summary of: Assignment of the relative stereochemistry of two novel vicinal dibromo compounds using NMR and DFT-GIAO calculations, Journal of Molecular Structure, July 2020, Elsevier, DOI: 10.1016/j.molstruc.2020.128157.
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