Synthesis of Tricyclopolyprenols via a Radical Addition and a Stereoselective Elimination. Part 1. Methodology. -Based on smooth radical addition of the alkenes (III) to the iodide (II) without radical rearrangement, stereoselective elimination of H 2 O from the activated alcohols (V) and (IX), and
Synthesis of vinylic and cyclic sulfones via a radical addition-elimination sequence
β Scribed by Albert Padwa; S.Shaun Murphree; Philip E. Yeske
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 253 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Radical attack on the double bond of 2,3-bis(phenylsulfonyl)-1 -propene leads to an intermediate sulfonyl stabilized radical. This species readily fragments to produce a new vinyl sulfone which can undergo further radical cyclization to give a six ring sulfone.
π SIMILAR VOLUMES
Cerium-mediated conjugate additions of (diethoxyphosphinoyl)difluoromethyllithium to cyclic vinyl sulfones proceeded smoothly; reduction afforded the products of formal alkylation, attaching the difluoromethylene phosphonate group to a secondary carbon atom. With acyclic vinyl sulfones, the addition