Synthesis of medium-bridged twisted lactams via cation-π control of the regiochemistry of the intramolecular Schmidt reaction was written by Szostak, Michal;Yao, Lei;Aube, Jeffrey. And the article was included in Journal of Organic Chemistry in 2010.Computed Properties of C4H8ClI This article mentions the following:
Medium-bridged twisted amides can be synthesized i. e., I by the intramol. Schmidt reaction of 2-azidoalkyl ketones. In these reactions, the regiochem. of the Schmidt reaction is diverted into a typically disfavored pathway by the presence of an aromatic group at the α-position adjacent to the ketone, which stabilizes the predominantly reactive conformation of the azidohydrin intermediate by engaging in a nonbonded cation-π interaction with the pos. charged diazonium cation. This results in the rarely observed rearrangement of the C-C bond distal to the azidoalkyl chain. This reaction pathway also requires the azide-containing tether to be situated in the axial orientation in the key azidohydrin intermediate. Examination of the effect of substitution of aromatic rings on the regiochem. of the Schmidt reaction shows an increase in the migratory selectivity with more electron-rich aromatic groups. The selectivity is lower when an electron-withdrawing substituent is placed on the aromatic ring. The ability of cation-π interactions to act as a controlling element decreases when Lewis acids coordinate to substituents on the aromatic ring. The developed version of the Schmidt reaction provides a direct access to a family of medium-bridged twisted amides with a [4.3.1] bicyclic system, compounds which are very difficult to access with use of other currently available methods. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Computed Properties of C4H8ClI).
1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Computed Properties of C4H8ClI
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com