113335-75-4Relevant academic research and scientific papers
Radical Deuteration with D2O: Catalysis and Mechanistic Insights
Soulard, Valentin,Villa, Giorgio,Vollmar, Denis Patrick,Renaud, Philippe
, p. 155 - 158 (2018)
Selective incorporation of deuterium atoms into molecules is of high interest for labeling purposes and for optimizing properties of drug candidates. A mild and environmentally benign method for the deuteration of alkyl iodides via radical pathway using D2O as source of deuterium has been developed. The reaction is initiated and mediated by triethylborane in the presence of dodecanethiol as a catalyst. This method is compatible with a wide range of functional groups and provides the monodeuterated products in good yields and with a high level of deuterium incorporation. It opens promising opportunities for the development of enantioselective radical reactions. Moreover, a revision of the mechanism of the deoxygenation reaction of xanthates using R3B and water (Wood deoxygenation) is presented.
Effect of Temperature on Atom Transfer Cyclization Reactions of Allylic α-Iodo Esters and Amides
Curran, Dennis P.,Tamine, John
, p. 2746 - 2750 (2007/10/02)
Atom-transfer cyclizations of allyl iodoacetates and N-allyl-N-methyliodoacetamides are much more efficient at 80 deg C than at 25 deg C.At 80 deg C, β-(iodomethyl) lactones and lactams are formed rapidly and in good yield under standard atom-transfer conditions (sunlamp irradiation of iodide and 10percent hexabutylditin in benzene for 10-60 min).It is proposed that this temperature effect is responsible for some unusual observations by Jolly and Livinghouse in the cyclization of N-cyclohexenyl-N-methyliodoacetamide.The results suggest that the beneficial effect of temperature arises because an increase in the rate of rotation of t he OC-O or OC-N bond in the intermediate radicals begins to convert syn radicals (which cannot cyclize) to anti radicals (which can cyclize).Consistent with this hypothesis, the radical derived from N,N-diallyliodoacetamide (which always has a favorable arrangement for cyclization) closes with excellent efficiency at 25 deg C.
