Radical β-addition to acyclic α-(arylsulfinyl) enones: Pummerer-type rearrangement

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Nobuyuki Mase, Yoshihiko Watanabe, Yoshio Ueno and Takeshi Toru


Abstract

The reaction of (S,E[hair space])-3-([hair space]p-tolylsulfinyl)pent-3-en-2-one with an isopropyl radical, generated from isopropyl iodide and triethylborane, gives the non-stereoselective addition product and an unexpected α-(arylsulfanyl) enone which is formed through a radical addition and subsequent Pummerer-type rearrangement. The formation of the α-(arylsulfanyl) enone depends upon the additives used as well as the aryl group on the sulfur.


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