Radical β-addition to acyclic α-(arylsulfinyl) enones: Pummerer-type rearrangement
- 1 January 1998
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1613-1618
- https://doi.org/10.1039/a800828k
Abstract
The reaction of (S,E)-3-(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.Keywords
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