1237739-82-0Relevant articles and documents
Alkene hydrofunctionalization using hydroxamic acids: A radical-mediated approach to alkene hydration
Giglio, Benjamin C.,Alexanian, Erik J.
supporting information, p. 4304 - 4307 (2014/11/07)
A radical-mediated approach to alkene hydration is described. The present strategy capitalizes on the unique radical reactivity of hydroxamic acids, which are capable of functioning as both synthetically useful oxygen-centered radical species and suitable hydrogen atom-based donors. This reaction manifold has been applied to both alkene hydrations and tandem alkene-alkene carbocyclization processes.
Metal-free oxyaminations of alkenes using hydroxamic acids
Schmidt, Valerie A.,Alexanian, Erik J.
, p. 11402 - 11405 (2011/09/16)
A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.
Metal-free, aerobic dioxygenation of alkenes using hydroxamic acids
Schmidt, Valerie A.,Alexanian, Erik J.
supporting information; experimental part, p. 4491 - 4494 (2010/08/21)
(Chemical equation presented) One dioxygenation please, hold the metal: In the presence of either oxygen or air as the sole oxidant and external oxygen atom source, a variety of unsaturated hydroxamic acids afford cyclic hydroxamates that are readily converted into 1,2-diols, with the potential for high levels of reaction stereocontrol.
