Reaction of 3-alkenols with thallium trinitrate: An unexpected and useful ring contraction

Authors
Ferraz, HMC Santos, AP Silva, LF Vieira, TD
Citation
Hmc. Ferraz et al., Reaction of 3-alkenols with thallium trinitrate: An unexpected and useful ring contraction, SYN COMMUN, 30(4), 2000, pp. 751-762
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
4
Year of publication
2000
Pages
751 - 762
Database
ISI
SICI code
0039-7911(2000)30:4<751:RO3WTT>2.0.ZU;2-J
Abstract
The first thallium trinitrate (TTN) mediated ring contraction of cyclic hom oallylic alcohols, using a 1:1 mixture of AcOH and H2O as solvent, is descr ibed. The reaction or two of these alcohols with excess of TTN in pentane g ave alpha-spirocyclopentyl-gamma-butirolactones in reasonable yields.