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Hunsdiecker Reaction

Several reviews have been published, and a catalytic approach has been developed. In particular, Chowdhury and Roy noted several drawbacks of using Hunsdiecker reaction, namely that some reagents, such as molecular bromine and salts of mercury, thallium, lead, and silver, are inherently toxic and that reactions with α, β-unsaturated carboxylic acids result in low yield. Regarding reactions using α, β-unsaturated carboxylic acids, Kuang et al. modified the reaction with using a new halogenating agent, N-halosuccinimide, and lithium acetate as the catalyst, which resulted in higher yield of β-Halostyrenes. They found that using the microwave irradiation could synthesize (E)-β-arylvinyl halide much quicker with higher yields. This is useful because synthesizing (E)-vinyl bromide in general is not very practical due to the complexity of alternative reagents (e.g. organometallic compounds), longer reaction times, and lower yields. Using microwave irradiation also allows the synthesized arylvinyl halide to carry electron-donating groups (in addition to electron-withdrawing groups), which is not possible with alternative synthetic methods. It was noted that lithium acetate resulted in higher yields compared to other relatively complex catalysts (e.g. tetrabutylammonium trifluoroacetate).