270901-39-8Relevant academic research and scientific papers
CO-trapping reaction under thermolysis of alkoxyamines: Application to the synthesis of 3,4-cyclopenta-1-tetralones
Uenoyama, Yoshitaka,Tsukida, Masaaki,Doi, Takashi,Ryu, Ilhyong,Studer, Armido
, p. 2985 - 2988 (2005)
(Chemical Equation Presented) An efficient one-pot sequence comprising a PRE-mediated radical 5-exo-cyclization, a radical carbonylation, a nitroxide trapping reaction, and a subsequent acid-catalyzed Friedel-Craft-type acylation provides a new entry into
Factors influencing the C-O bond homolysis of alkoxyamines: Effects of H-bonding and polar substituents
Marque,Fischer,Baier,Studer
, p. 1146 - 1156 (2007/10/03)
The synthesis of various new trialkylhydroxylamines is described. The rate constant of the C-O bond cleavage of these new alkoxyamines has been measured. For example, C-O bond homolysis rates in a series of para-substituted TEMPO-styryl compounds TEMPO-CH(CH3)C6H5X 1a (p-MeO), 1b (p-Me), 1d (p-H), 1e (p-Br), and 1f (p-MeO2C) are presented. Furthermore, rate constants for the C-O bond cleavage of α-heteroaryl-substituted secondary alkoxyamines are discussed. A correlation by which the rate constant for the C-O bond cleavage of TEMPO-derived alkoxyamines can be predicted from the C-H BDEs of the corresponding alkanes is presented. Solvent effects as well as the effect of camphorsulfonic acid on the rate of the C-O bond homolysis are discussed. Finally, EPR and kinetic evidence show that alkoxyamines derived from nitroxides which are capable of intramolecular H-bonding undergo C-O bond cleavage faster than the corresponding non-H-bond-forming analogues.
