Secondary Amides as Hydrogen Atom Transfer Promoters for Reactions of Samarium Diiodide.

Title Secondary Amides as Hydrogen Atom Transfer Promoters for Reactions of Samarium Diiodide.
Authors T.V. Chciuk; A.M. Li; A. Vazquez-Lopez; W.R. Anderson; R.A. Flowers
Journal Org Lett
DOI 10.1021/acs.orglett.6b03664
Abstract

Two secondary amides (N-methylacetamide and 2-pyrrolidinone) were used as additives with SmI2 in THF to estimate the extent of N-H bond weakening upon coordination. Mechanistic and synthetic studies demonstrate significant bond-weakening, providing a reagent system capable of reducing a range of substrates through formal hydrogen atom transfer.

Citation T.V. Chciuk; A.M. Li; A. Vazquez-Lopez; W.R. Anderson; R.A. Flowers.Secondary Amides as Hydrogen Atom Transfer Promoters for Reactions of Samarium Diiodide.. Org Lett. 2017;19(1):290293. doi:10.1021/acs.orglett.6b03664

Related Elements

Samarium

See more Samarium products. Samarium (atomic symbol: Sm, atomic number: 62) is a Block F, Group 3, Period 6 element with an atomic radius of 150.36. Samarium Bohr ModelThe number of electrons in each of samarium's shells is 2, 8, 18, 24, 8, 2 and its electron configuration is [Xe]4f6 6s2. The samarium atom has a radius of 180 pm and a Van der Waals radius of 229 pm. In its elemental form, samarium has a silvery-white appearance. Elemental Samarium PictureSamarium is not found as free element in nature. It is found in the minerals cerite, gadolinite, samarskite, monazite and bastnäsite. Samarium is classified as a rare earth element and is the 40th most abundant element in the Earth's crust. Samarium was discovered and first isolated by Lecoq de Boisbaudran in 1879. It is named after the mineral samarskite, the mineral from which it was isolated.

Iodine

See more Iodine products. Iodine (atomic symbol: I, atomic number: 53) is a Block P, Group 17, Period 5 element with an atomic radius of 126.90447. The number of electrons in each of Iodine's shells is 2, 8, 18, 18, 7 and its electron configuration is [Kr] 4d10 5s2 5p5. The iodine atom has a radius of 140 pm and a Van der Waals radius of 198 pm. In its elemental form, iodine has a lustrous metallic gray appearance as a solid and a violet appearance as a gas or liquid solution. Elemental IodineIodine forms compounds with many elements, but is less active than the other halogens. It dissolves readily in chloroform, carbon tetrachloride, or carbon disulfide. Iodine compounds are important in organic chemistry and very useful in the field of medicine. Iodine was discovered and first isolated by Bernard Courtois in 1811. The name Iodine is derived from the Greek word "iodes" meaning violet.

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