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Tandem: Allylic alcohols react with N-chlorosuccinimide (NCS) in a tandem 1,3-H shift/CCl bond formation leading to α-chloroketones and α-chloroaldehydes. The reactions proceed with complete selectivity to give single constitutional isomers of monochlorinated carbonyl compounds. The utility of the transformation is illustrated by the straightforward synthesis of 4,5-disubstituted 2-aminothiazoles from allylic alcohols.
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Ahlsten et al. (2013) studied this question.
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