A convenient preparation of sulfuryl chloride fluoride

Reddy, V. Prakash; Bellew, Donald R.; Prakash, G. K. Surya

doi:10.1016/s0022-1139(00)81102-1

Cited by 45 publications

(13 citation statements)

References 9 publications

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“…[17] Sulfur dioxide was obtained from Matheson Gas Products Inc.a nd was purified by trap-to-trap distillation. SO 2 ClF was synthesized according to known methods [18] and purified by distillationatlow temperature under argon several times,and then stored over P 2 O 5 in aS chlenk tube.…”

Section: Methodsmentioning

confidence: 99%

Features of Protonation of the Simplest Weakly Basic Molecules, SO₂, CO, N₂O, CO₂, and Others by Solid Carborane Superacids

Stoyanov

Stoyanova

2018

Angew Chem Int Ed

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An experimental study on protonation of simple weakly basic molecules (L) by the strongest solid superacid, H(CHB F ), showed that basicity of SO is high enough (during attachment to the acidic H atoms at partial pressure of 1 atm) to break the bridged H-bonds of the polymeric acid and to form a mixture of solid mono- LH ⋅⋅⋅An , and disolvates, L-H -L. With a decrease in the basicity of L=CO (via C), N O, and CO (via O), only proton monosolvates are formed, which approach L-H -An species with convergence of the strengths of bridged H-bonds. The molecules with the weakest basicity, such as CO and weaker, when attached to the proton, cannot break the bridged H-bond of the polymeric superacid, and the interaction stops at stage of physical adsorption. It is shown here that under the conditions of acid monomerization, it is possible to protonate such weak bases as CO , N , and Xe.

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Section: Methodsmentioning

confidence: 99%

Features of Protonation of the Simplest Weakly Basic Molecules, SO₂, CO, N₂O, CO₂, and Others by Solid Carborane Superacids

Stoyanov

Stoyanova

2018

Angew Chem Int Ed

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“…Inspired by the report of Prakash, sulfuryl chloride fluoride was selected as our first candidate. 23 Therein, the SO 2 ClF gas could selectively be formed from sulfuryl chloride and a fluoride source in acidic medium and subsequently be isolated after gas condensation, albeit in low yield. We assumed that translating this work to a two-chamber reactor 24 would significantly improve this method, as the generated gas can migrate to an adjacent chamber, where it is directly consumed thus avoiding intermediate isolation.…”

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confidence: 99%

Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

et al. 2017

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A convenient transformation of phenols into the corresponding aryl fluorosulfates is presented: the first protocol to completely circumvent direct handling of gaseous sulfuryl fluoride (SOF). The proposed method employs 1,1'-sulfonyldiimidazole as a precursor to generate near-stoichiometric amounts of SOF gas using a two-chamber reactor. With NMR studies, it was shown that this ex situ gas evolution is extremely rapid, and a variety of phenols and hydroxylated heteroarenes were fluorosulfated in good to excellent yields.

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“…We commenced our study with the screening of suitable FSO 2 radical precursors in the form of FSO 2 ‐X that might be able to generate the FSO 2 radical under photoredox conditions [12] . Even though no desired product was observed in the reactions of styrene with FDIT and a series of fluorosulfates, we finally found sulfuryl chlorofluoride (FSO 2 Cl), [13] could afford the desired radical fluorosulfonylation product, albeit in low yield. Surprisingly, a large number of chlorinated by‐products were detected by GC‐MS analysis (for details, see Table S1).…”

Section: Figurementioning

confidence: 77%

Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes

Nie

Song

et al. 2020

Angew Chem Int Ed

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Sulfonyl fluorides have widespread applications in many fields. In particular, their unique biological activity has drawn considerable research interest in the context of chemical biology and drug discovery in the past years. Therefore, new and efficient methods for the synthesis of sulfonyl fluorides are highly in demand. In contrast to extensive studies on FSO2+‐type reagents, a radical fluorosulfonylation reaction with a fluorosulfonyl radical (FSO2.) remains elusive so far, probably owing to its instability and difficulty in generation. Herein, the development of the first radical fluorosulfonylation of alkenes based on FSO2 radicals generated under photoredox conditions is reported. This radical approach provides a new and general access to alkenyl sulfonyl fluorides, including structures that would otherwise be challenging to synthesize with previously established cross‐coupling methods. Moreover, extension to the late‐stage fluorosulfonylation of natural products is also demonstrated.

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A convenient preparation of sulfuryl chloride fluoride

Cited by 45 publications

References 9 publications

Features of Protonation of the Simplest Weakly Basic Molecules, SO₂, CO, N₂O, CO₂, and Others by Solid Carborane Superacids

Features of Protonation of the Simplest Weakly Basic Molecules, SO₂, CO, N₂O, CO₂, and Others by Solid Carborane Superacids

Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes

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A convenient preparation of sulfuryl chloride fluoride

Cited by 45 publications

References 9 publications

Features of Protonation of the Simplest Weakly Basic Molecules, SO2, CO, N2O, CO2, and Others by Solid Carborane Superacids

Features of Protonation of the Simplest Weakly Basic Molecules, SO2, CO, N2O, CO2, and Others by Solid Carborane Superacids

Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes

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Features of Protonation of the Simplest Weakly Basic Molecules, SO₂, CO, N₂O, CO₂, and Others by Solid Carborane Superacids

Features of Protonation of the Simplest Weakly Basic Molecules, SO₂, CO, N₂O, CO₂, and Others by Solid Carborane Superacids