Mn-Mediated Coupling of Alkyl Iodides and Chiral N-Acylhydrazones: Optimization, Scope, and Evidence for a Radical Mechanism was written by Friestad, Gregory K.;Marie, Jean-Charles;Suh, YoungSung;Qin, Jun. And the article was included in Journal of Organic Chemistry in 2006.Product Details of 10297-05-9 This article mentions the following:
Stereoselective radical additions have excellent potential as mild, nonbasic carbon-carbon bond constructions for direct asym. amine synthesis. Efficient intermol. radical addition to C:N bonds with acyclic stereocontrol has previously been limited mainly to secondary and tertiary radicals, a serious limitation from the perspective of synthetic applications. Here, we provide full details of the use of photolysis with manganese carbonyl to mediate stereoselective intermol. radical addition to N-acylhydrazones. Photolysis (300 nm) of alkyl halides and hydrazones in the presence of Mn2(CO)10 and InCl3 as a Lewis acid led to reductive radical addition; diastereomer ratios ranged from 93:7 to 98:2 at ca. 35 鎺矯. The reaction tolerates addnl. functionality in either reactant, enabling subsequent transformations as shown in an efficient asym. synthesis of coniine. A series of hydrazones bearing different substituents on the oxazolidinone auxiliary were compared; consistently high diastereoselectivity revealed that the identity of the substituent had little practical effect on the diastereoselectivity. Further mechanistic control experiments confirmed the intermediacy of radicals and showed that independently prepared alkyl- or acyl manganese pentacarbonyl compounds do not undergo efficient addition to the N-acylhydrazones under thermal or photolytic (300 nm) conditions. These Mn-mediated conditions avoid toxic tin reagents and enable stereoselective intermol. radical additions to C:N bonds with the broadest range of alkyl halides yet reported, including previously ineffective primary alkyl halides. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Product Details of 10297-05-9).
1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Product Details of 10297-05-9
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com