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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.
