69442-38-2Relevant academic research and scientific papers
Chemical and Biological Oxidation of Organohalides. Peracid Oxidation of Alkyl Iodides
Macdonald, Timothy L.,Narasimhan, N.,Burka, Leo T.
, p. 7760 - 7765 (1980)
The peracid oxidation of seven alkyl iodides has been examined in nonpolar solvents.The stoichiometry for the reaction is shown to be (8 + n)ArCO3H + 6RI + 3H2O -> (8 + n)ArCO2H + 6ROH + 2I2 + I2O5 + (n/2)O2 (R = n-heptyl, Ar = m-ClC6H4, n = 4-16).Evidence is presented for the intermediacy of an alkyliodosyl compound in these oxidations.Primary alkyl iodides give exclusively displacement products, whereas secondary iodides give a mixture of products resulting from displacement, elimination, and α-carbon oxidation.Tertiary iodides give products resulting form displacement and elimination.Mechanisms for the formation of these products are presented.The overall rate of peracid mediated reaction is dependent upon the alkyl group: tertiary > secondary > methyl primary iodides.The bioactivation of organohalides via an analogous halogen oxidation process is discussed.
Generally applicable and efficient esterification of aldehydes with alcohols catalyzed by cyclopalladated ferrocenylimine
Ma, Gaizhi,Leng, Yuting,Qiao, Huijie,Yang, Fan,Wang, Shiwei,Wu, Yangjie
, p. 44 - 47 (2014/01/06)
The palladacycle-catalyzed esterification of a variety of aldehydes with alcohols was developed. This reaction allows formation of esters in moderate to excellent yields not only for various aldehydes but also alcohols. In addition, the esterification could proceed well under mild conditions with a low catalyst loading of 0.0625 mol%. Copyright
Oxidative Displacement of Hypervalent Iodine from Alkyl Iodides
Cambie, Richard C.,Chambers, David,Lindsay, Barry G.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 822 - 827 (2007/10/02)
Oxidative displacement of iodine from primary alkyl iodides and vic-substituted iodocyclohexanes with m-chloroperbenzoic acid in either dichloromethane or t-butyl alcohol-water gives primary alcohols and vic-substituted cyclohexanols, respectively.Retention of configuration at the displacement centre occurs for all of the trans-vic-substituted iodocyclohexanes except the iodoacetate and iodotrifluoroacetate where inversion of configuration occurs to give cis-hydroxy-esters.Oxidation of (S)-2-iodo-octane occurs with almost complete inversion to give (R)-octan-2-ol but also affords octan-1-ol, octan-3-ol, and octan-2-one.
