1809-05-8Relevant articles and documents
NaIO4-KI-NaN3 as a new reagent system for C-H functionalization in hydrocarbons
Chouthaiwale, Pandurang V.,Suryavanshi, Gurunath,Sudalai, Arumugam
scheme or table, p. 6401 - 6403 (2009/04/06)
The NaIO4-KI-NaN3 combination has been found to be an efficient, reliable, and inexpensive reagent system for mono- and 1,2-difunctionalization of hydrocarbons via C-H bond activation to afford vicinal azido- and acetoxy iodinations of cyclic hydrocarbons.
Direct bromination and iodination of non-activated alkanes by hypohalite reagents
Montoro, Raul,Wirth, Thomas
, p. 1473 - 1478 (2007/10/03)
The direct functionalisation of alkanes through bromination and iodination has been successfully achieved. The combination of stoichiometric mixtures of elemental halogen and sodium alkoxides leads to the formation of alkyl hypobromites and hypoiodites as reagents. The halogenation occurs without external photostimulation under thermal reaction conditions. Georg Thieme Verlag Stuttgart.
Mechanism of decomposition of quasiphosphonium intermediates: Borderline SN1 character of alkyl-oxygen fission in sec-alkyloxyphosphonium salts
Hudson,Qureshi
, p. 473 - 480 (2007/10/03)
Short-lived alkoxyphosphonium intermediates have been detected in the interactions of alkyl diphenylphosphinites ROPPh2 (R = Et, Pr i, Bu8, and 3-pentyl) with iodomethane at room temperature. Phosphorus chemical shifts for the sec-alkoxy(methyl) diphenylphosphonium iodides (δp 68.6-68.7 ppm) are at slightly higher field than for ethoxy(methyl)diphenylphosphonium iodide (δp 72.4 ppm), in accord with higher electron density at phosphorus in the secondary alkyl sytems. Relative rates of decomposition in CDCl3 (Me > Et > Pri ? neopentyl) are in accord with SN2-type cleavage of the R-O bond but within the secondary alkyl series the relative rates (Pri 8 N1 mechanism is proposed.