Sulfuryl Chloride in Organic Chemistry

Brown, Herbert C.

doi:10.1021/ie50417a003

Cited by 16 publications

(11 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 1980, sulfuryl chloride was used as a source of chlorine and solvent in the synthesis of [B 9 Cl 9 ] 2– . Sulfuryl chloride is less hazardous, cheaper, and easier to handle than chlorine gas and has been successfully applied as a chlorinating agent in organic chemistry. , To achieve chlorination in boron clusters, solubilization of the cesium and tetramethylammonium (the most common) salts of the different boron clusters was needed, but these are not fully soluble in sulfuryl chloride. In 2010, a step forward was achieved by mixing acetonitrile with sulfuryl chloride to increase the solubility.…”

Section: Resultsmentioning

confidence: 99%

1.3 V Inorganic Sequential Redox Chain with an All-Anionic Couple 1–/2– in a Single Framework

et al. 2021

View full text Add to dashboard Cite

The relatively low symmetry of [3,3′-Co(1,2-C 2 B 9 H 11 ) 2 ] − ([ 1 ] − ), along with the high number of available substitution sites, 18 on the boron atoms and 4 on the carbon atoms, allows a fairly regioselective and stepwise chlorination of the platform and therefore a very controlled tuning of the electrochemical potential tuning. This is not so easily found in other systems, e.g., ferrocene. In this work, we show how a single platform with boron and carbon in the ligand, and only cobalt can produce a tuning of potentials in a stepwise manner in the 1.3 V range. The platform used is made of two icosahedra sharing one vertex. The E 1/2 tuning has been achieved from [ 1 ] − by sequential chlorination, which has given potentials whose values increase sequentially and linearly with the number of chloro groups in the platform. [ Cl 8 -1 ] − , [ Cl 10 -1 ] − , and [ Cl 12 -1 ] − have been obtained, which are added to the existing [ Cl-1 ] − , [ Cl 2 -1 ] − , [ Cl 4 -1 ] − , and [ Cl 6 -1 ] − described earlier to give the 1.3 V range. It is envisaged to extend this range also sequentially by changing the metal from cobalt to iron. The last successful synthesis of the highest chlorinated derivatives of cobaltabis(dicarbollide) dates back to 1982, and since then, no more advances have occurred toward more substituted metallacarborane chlorinated compounds. [ Cl 8 -1 ] − , [ Cl 10 -1 ] − , and [ Cl 12 -1 ] − are made with an easy and fast method. The key point of the reaction is the use of the protonated form of [Co(C 2 B 9 H 11 ) 2 ] − , as a starting material, and the use of sulfuryl chloride, a less hazardous and easier to use chlorinating agent. In addition, we present a complete, spectroscopic, crystallographic, and electrochemical characterization, together with a study of the influence of the chlorination position in the electrochemical properties.

show abstract

Section: Resultsmentioning

confidence: 99%

1.3 V Inorganic Sequential Redox Chain with an All-Anionic Couple 1–/2– in a Single Framework

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[17,18] Chlorination of cyclohexene with sulfuryl chloride proceeds in excellent yield compared with alternative chlorinating agents such as Cl 2 , [19] PCl 5 , [20] PhICl 2 , [21] and MoCl 5 [22] (Scheme 7). Additionally, sulfuryl chloride is much cheaper to purchase than these reagents.…”

Section: Chlorination Of Alkenesmentioning

confidence: 99%

Sulfuryl Chloride: A Versatile Alternative to Chlorine

Moussa¹

2012

Aust. J. Chem.

View full text Add to dashboard Cite

“…1,2 In organic synthesis; they are primarily used as chlorination reagents, 2,3 while the reactivity of their respective cyclic sulfodiester derivatives is often compared with that of epoxides. 4,5 One limitation to the use of SOCl 2 and SO 2 Cl 2 arises from their high reactivity towards moisture.…”

Section: Introductionmentioning

confidence: 99%