20697-49-8Relevant academic research and scientific papers
Mechanism and scope of the base-induced dehalogenation of (E)-diiodoalkenes
Resch, Daniel,Lee, Chang Heon,Tan, Siew Yoong,Luo, Liang,Goroff, Nancy S.
, p. 730 - 737 (2015/01/30)
A wide range of nucleophiles have induced the elimination of iodine from (E)-diiodoalkenes to form alkynes under surprisingly mild conditions. The iodide anion is particularly efficient, and can drive the reaction to completion in less than 1 hour at room temperature in a polar aprotic solvent. Detailed investigations have suggested the reaction has a bimolecular polar mechanism. The deiodination reaction can be driven to completion with 1 equiv. of nucleophile and is partially catalytic with substoichiometric amounts of deiodinating reagent. Kinetic analysis of the stoichiometric iodide-induced reaction indicated an overall pseudo-first-order behavior. The reaction exhibited strong solvent effects, with much slower reactions observed in protic solvents than in polar aprotic solvents. The substrate dimethyl (2E)-2,3-diiodo-butene-2-dioate demonstrated orthogonal reactivity for either elimination or hydrolysis, depending on the solvent and nucleophile used. This reaction is a major pathway for all the diiodoalkenes examined, and represents a challenge and an opportunity for using these substrates in organic synthesis.
Iodoxolone-based hypervalent iodine reagents
Shah, Azhar-Ul-Haq A.,Khan, Zulfiqar A.,Choudhary, Naila,Lohoelter, Christine,Schaefer, Sascha,Marie, Guillaume P.L.,Farooq, Umar,Witulski, Bernhard,Wirth, Thomas
supporting information; experimental part, p. 3578 - 3581 (2011/02/22)
Image Persented The fast access to simple (Z)-3-iodo acrylic acid derivatives which can be easily oxidized to the corresponding hypervalent iodine(III) reagents is described. They can be used for various reactions with superior or similar reactivity as conventional hypervalent iodine(III) reagents.
