Synthesis and Nuclear Magnetic Resonance Spectra of Some 1-Halo-1-iodoalkanes

Abstract

The previously unknown symmetrical dihalides 1,l-diiodopropane and l,l-diiodo-2-methylpropane, have been synthesized by treatment of the corresponding diazoalkane with iodine. The new asymmetrical dihalides, 1-chloro-1-iodopropane and 1-bromo-1-iodopropane, have been obtained by halodecarboxylation of a-chlorobutyric and a-bromobutyric acid, respectively, with lead tetraacetate in the presence of iodine. Nmr spectral data for these and other geminal dihalides are presented and discussed.

Fragmentation of Carbohydrate Anomeric Alkoxy Radicals: A New Synthesis of Chiral 1-Halo-1-iodo Compounds

“…Consequently, in the majority of cases the 1,1‐diiodoalkanes obtained are derivatives of relatively simple hydrocarbons 3. A similar situation is found for the synthesis of mixed halo‐iodo species, for example 1‐fluoro‐1‐iodo,4 1‐chloro‐1‐iodo,5 and 1‐bromo‐1‐iodo compounds 6. Moreover, there are sufficient drawbacks to most of these procedures to justify the need for a general and practical method of generating these types of compounds under mild conditions.…”

Enantioselective assembly of tertiary stereocenters via multicomponent chemoselective cross-coupling of geminal chloro(iodo)alkanes

“…However, the development of their chemistry has been an uneven process, most likely, due to the lack of selective, practical and high yielding methods of their synthesis. 10 Recently, we reported a robust, general and efficient method for synthesis of alkyl iodides from carboxylic acids through their simple treatment with commercially available 1,3-diiodo-5,5-dimethylhydantoin (DIH) under visible light (VIS) irradiation. 11 We now report that, contrary to other iododecarboxylation approaches, 10 d our method can be uniquely extended to α-chloroalkanoic acids.…”

Decarboxylative Halogenation of Organic Compounds

“…Thus, α-chloroamide 169 and 2-chloro-oxetane 170 derivatives were successfully prepared. The synthesis of germinal iodo,chloro- and iodo,bromoalkanes was attempted via iododecarboxylation of α-chloro and α-bromopropionic acids under Barton conditions . However, the yields of these products were substantially low ( 186 – 188 ).…”