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 34-76%. 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 ω-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.
TY - JOUR
AU - Čeković, Živorad
AU - Đokić, Gordana
PY - 1981
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4418
AB - 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 34-76%. 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 ω-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.
PB - Elsevier
T2 - Tetrahedron
T1 - Ferrous ion induced decomposition of alkyl hypochlorites
VL - 37
IS - 24
SP - 4263
EP - 4268
DO - 10.1016/0040-4020(81)85021-1
ER -
@article{
author = "Čeković, Živorad and Đokić, Gordana",
year = "1981",
abstract = "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 34-76%. 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 ω-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.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Ferrous ion induced decomposition of alkyl hypochlorites",
volume = "37",
number = "24",
pages = "4263-4268",
doi = "10.1016/0040-4020(81)85021-1"
}
Čeković, Ž.,& Đokić, G.. (1981). Ferrous ion induced decomposition of alkyl hypochlorites. in Tetrahedron
Elsevier., 37(24), 4263-4268.
https://doi.org/10.1016/0040-4020(81)85021-1
Čeković Ž, Đokić G. Ferrous ion induced decomposition of alkyl hypochlorites. in Tetrahedron. 1981;37(24):4263-4268.
doi:10.1016/0040-4020(81)85021-1 .
Čeković, Živorad, Đokić, Gordana, "Ferrous ion induced decomposition of alkyl hypochlorites" in Tetrahedron, 37, no. 24 (1981):4263-4268,
https://doi.org/10.1016/0040-4020(81)85021-1 . .
