31598-76-2Relevant academic research and scientific papers
SUBSTITUENT-DIRECTED OXIDATION: REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE ADDITION OF HYPERVALENT IODINE REAGENTS TO CYCLOALKENOLS.
Kim, Ho-jin,Schlecht, Matthew F.
, p. 5229 - 5232 (1987)
The transannular oxidative cyclization of 1-methylcyclooct-4-en-1-ol and cyclooct-4-en-1-ol was studied using hypervalent iodine reagents.The regioselectivity for the vs. 9-oxabicyclononane skeletons is low, but the additions is highly trans-selective; the results are rationalized in terms of a tricyclic oxonium ion intermediate.
Heterolytic Oxygen-Oxygen Bond Formation via gem-Dialkylperoxonium Ions
Best, Stephen P.,Bloodworth, A. J.,Spencer, Michael D.
, p. 416 - 418 (2007/10/02)
Different extents of decomposition for the cis and trans isomers of 4,5-epoxycyclo-octyl hydroperoxide coupled with the formation of oxygen (identified by Raman spectroscopy) and bicyclic ethers suggest a mechanism involving the heterolytic formation of protonated alkyl hydrotrioxides by nucleophilic attack of hydroperoxide on gem-dialkylperoxonium ions.
