'Ole in one! Treatment of β-amino alcohols with CS2 under alkaline conditions gave 1,3-thiazolidine-2-thiones, which were then treated with benzyne generated in situ. The reaction underwent an unprecedented addition–elimination process to give the desired olefins in 60–87 % yields (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene).
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Hwu et al. (2011) studied this question.
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