68705-91-9Relevant academic research and scientific papers
SELECTIVITY OF TETRAHYDROFURAN FORMATION FROM UNACTIVATED ALIPHATIC ALCOHOLS BY THE BROMINE-SILVER-SALT REACTION
Roscher, Nina Matheny,Shaffer, D. Kent
, p. 2643 - 2650 (2007/10/02)
Studies of the bromine-silver carbonate reaction with aliphatic alcohols in which intramolecular δ-H competition is possible are generally quite specific.Loss of a tertiary δ- hydrogen occurs preferentially from both tertiary and secondary aliphatic alcohols to yield the most highly substituted cyclic ether.For example, 2,5-dimethyl-2-octanol yields only 2,2,5-trimethyl-5-propyltetrahydrofuran as the cyclic ether product; 2-methyl-2-isopentyltetrahydrofuran is not detected.
FERROUS ION INDUCED DECOMPOSITION OF ALKYL HYPOCHLORITES
Cekovic, Zivorad,Djokic, Gordana
, p. 4263 - 4268 (2007/10/02)
The decomposition of primary, secondary and tertiary alkyl hypochlorites induced by ferrous and other one-electron oxidizable metal ions leads to δ-chloro alcohols in yields of 34-76percent.In decomposition of tertiary alkyl hypochlorites, β-fragmentation competes with intramolecular δ-chlorination.Tertiary cycloalkyl hypochlorites containing five- or six-membered rings undergo β-cleavage giving the corresponding ο-chloro ketones, while 1-methylcycloheptyl and 1-methylcyclooctyl hypochlorites by decomposition with ferrous ion proceed by transannular functionalization of δ-carbon atom and β-cleavage as a competing reaction.
