119648-97-4Relevant academic research and scientific papers
Thallium trinitrate mediated oxidation of 3-alkenols: Ring contraction vs cyclization
Ferraz, Helena M. C.,Longo Jr., Luiz S.,Zukerman-Schpector, Julio
, p. 3518 - 3521 (2007/10/03)
The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.
Terpenoid Ether Formation in Superacids
Carr, Graham,Dean, Cristopher,Whittaker, David
, p. 351 - 354 (2007/10/02)
A number of terpenoid bicyclic ethers have been prepared by cyclisation of suitable precursors in fluorosulphuric acid-sulphur dioxide.The products are formed under a mixture of thermodynamic and kinetic control, and five-, and six-, and seven-membered-ring ethers are obtained.Both primary and secondary alcohols have been cyclised by attack of the hydroxy group on carbocation centres generated by protonation of alkenes or ionisation of tertiary alcohols; tertiary alcohols ionise too readily to provide an etheral oxygen atom.Reaction of the unsaturated secondary alcohol dihydrocarveol (2) with antimony pentafluoride in sulphur dioxide gives the ether by a reaction which may not involve a carbocation, and hence may be suitable for ether formation from substrates which rearrange readily in acids.
