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Alpha-lipoic acid can react with a variety of reagents, including:
* Electrophiles: Alpha-lipoic acid can react with electrophiles to form adducts. For example, it can react with alkyl halides to form alkylated alpha-lipoic acids. Alpha-lipoic acid can also react with aldehydes and ketones to form imines.
* Nucleophiles: Alpha-lipoic acid can react with nucleophiles to form addition products. For example, it can react with amines to form amides. Alpha-lipoic acid can also react with alkoxide ions to form esters.
* Oxidizing agents: Alpha-lipoic acid can be oxidized by a variety of oxidizing agents, including hydrogen peroxide and potassium permanganate. Oxidation of alpha-lipoic acid produces a variety of products, including dihydrolipoic acid and dehydrolipoic acid.
* Reducing agents: Alpha-lipoic acid can be reduced by a variety of reducing agents, including sodium borohydride and dithiothreitol. Reduction of alpha-lipoic acid produces dihydrolipoic acid.
The selectivity of these reactions depends on a variety of factors, including the reaction conditions, the concentration of the reactants, and the presence of catalysts.