Cyclization by Intramolecular Carbolithiation of Alkyl-and Vinyllithiums Prepared by the Action of Aromatic Radical Anions on Phenyl Thioethers. High Stereoselectivity …
The reductive lithiation of alkyl and vinyl phenyl thioethers by aromatic radical anions is shown to be the most general method yet known for preparing organolithiums capable of intramolecular carbometalation of unactivated alkenes to produce five-membered rings and in one case a four-membered ring (in a far higher yield than known cases). The relative rates of cyclization for alkyllithiums are secondary> tertiary> primary, and the yields are very ...
