203513-25-1Relevant articles and documents
Activation of Electron-Deficient Quinones through Hydrogen-Bond-Donor-Coupled Electron Transfer
Turek, Amanda K.,Hardee, David J.,Ullman, Andrew M.,Nocera, Daniel G.,Jacobsen, Eric N.
supporting information, p. 539 - 544 (2016/02/27)
Quinones are important organic oxidants in a variety of synthetic and biological contexts, and they are susceptible to activation towards electron transfer through hydrogen bonding. Whereas this effect of hydrogen bond donors (HBDs) has been observed for Lewis basic, weakly oxidizing quinones, comparable activation is not readily achieved when more reactive and synthetically useful electron-deficient quinones are used. We have successfully employed HBD-coupled electron transfer as a strategy to activate electron-deficient quinones. A systematic investigation of HBDs has led to the discovery that certain dicationic HBDs have an exceptionally large effect on the rate and thermodynamics of electron transfer. We further demonstrate that these HBDs can be used as catalysts in a quinone-mediated model synthetic transformation.
Altering the Stereochemistry of Allylation Reactions of Cyclic α-Sulfinyl Radicals with Diarylureas
Curran, Dennis P.,Kuo, Lung Huang
, p. 3259 - 3261 (2007/10/02)
Radical allylations of 2-(phenylseleno)tetrahydrothiophene oxide and 2-benzyl-5-(phenylseleno)-3-isothiazolidone 1-oxide with allyltributylstannane in the presence of N,N-bis urea have been investigated.This urea was shown to be about as selective as promoting formation of trans-2-allyltetrahydrothiophene oxide and trans-5-allyl-2-benzyl-3-isothiazolidone 1-oxide as hydrogen bonding solvents and Lewis acids.
