72978-95-1Relevant academic research and scientific papers
Dienediolates of unsaturated carboxylic acids in synthesis. Aldehydes and ketones from alkyl halides, by ozonolysis of β,γ-unsaturated α-alkyl carboxylic acids. The role of a tertiary amine in the cleavage of ozonides
Aurell, Maria Jose,Ceita, Luisa,Mestres, Ramon,Tortajada, Amparo
, p. 10883 - 10898 (2007/10/03)
A convenient two-step procedure for a two carbon homologative conversion of alkyl halides into aldehydes and methyl ketones by α-alkylation of unsaturated carboxylic acids, followed by ozonolysis is developed and applied to the synthesis of ω-chloro aldehydes. Triethylamine is superior to dimethyl sulfide or triphenylphosphine for cleavage of the ozonides, except when aldol condensation side reactions require use of protic solvents and iodide salts. Cleavage of the ozonides by triethylamine is shown to occur mainly through a reductive process.
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.
