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A series of gold(I)-catalyzed oxidative rearrangement reactions of alkynes using sulfoxides as stoichiometric oxidants are reported. The reactions are postulated to proceed through intermolecular oxygen atom transfer from the sulfoxide to gold(I)−carbenoid intermediates. Under the conditions for gold(I)-catalyzed oxidative rearrangement, 1,6-enynes are isomerized to cyclopropyl aldehydes, homopropargyl azides produce pyrrolones, acetylenic α-diazoketones form cyclic en-1,4-diones, and propargylesters produce 2-acyloxyenals.
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Witham et al. (2007) studied this question.
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