A Practical Chiral Bicyclic Thioglycolate Lactam Auxiliary for Stereoselective Quaternary Carbon Formation was written by Arpin, Azelie;Manthorpe, Jeffrey M.;Gleason, James L.. And the article was included in Organic Letters in 2006.Reference of 10297-05-9 This article mentions the following:
Chiral bicyclic thioglycolate lactams may be prepared in three steps from inexpensive com. materials. The resulting lactams may be alkylated three times, twice using basic enolization and once using reductive enolization, to form α-quaternary carboxylic acid derivatives in high yield and with high diastereoselectivity. The alkylation products may be cleaved under either acidic or reductive conditions to furnish either carboxylic acids or primary alcs., resp. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Reference of 10297-05-9).
1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Reference of 10297-05-9
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com