A new synthesis of alkane and polyfluoroalkanesulfonyl chlorides

Benfodda, Zohra; Guillen, F.; Arnion, Hélène; Dahmani, Abdelkader; Blancou, H.

doi:10.1002/hc.20559

Cited by 6 publications

(4 citation statements)

References 16 publications

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“…Thiocyanate groups can undergo oxidative chlorination and cleavage with sulfuryl chloride and form sulfonyl chlorides [16] . However, the use of sulfuryl chloride in boron cluster chemistry was reported rather in terms of effective polychlorination of various boron cages, in particular those bearing an anionic charge [17] .…”

Section: Resultsmentioning

confidence: 99%

“…Thiocyanate groups can undergoo xidativec hlorination and cleavage with sulfuryl chloride and form sulfonyl chlorides. [16] However,the use of sulfuryl chloride in boron clusterchemistry was reported rather in terms of effective polychlorination of variousb oron cages, in particulart hose bearing an anionic charge. [17] Nevertheless, when the reactions of neutrald icarbacloso-dodecaboranes were carried out at relativelym ild temperatures (up to 50 8C), no sign of clusterc hlorination was observed with either NMR spectroscopy or MS. All the reactions led to corresponding sulfonyl chlorides of the formula 1-ClSO 2 -(CH 2 ) 3 -C 2 B 10 H 11 (ortho-8, meta-8, para-8)a nd 1,2-, 1,7-, or 1,12-(ClSO 2 -(CH 2 ) 3 ) 2 -C 2 B 10 H 10 (ortho-9, meta-9, para-9), and the expected products were isolated in good yield.…”

Section: Chemistrymentioning

confidence: 99%

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Direct Introduction of an Alkylsulfonamido Group on C‐sites of Isomeric Dicarba‐closo‐dodecaboranes: The Influence of Stereochemistry on Inhibitory Activity against the Cancer‐Associated Carbonic Anhydrase IX Isoenzyme

Nekvinda

Kugler

Holub

et al. 2020

Chemistry A European J

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Carbonic anhydrase IX (CA IX), at umor-associated metalloenzyme, represents avalidated target for cancertherapy and diagnostics. Herein, we report the inhibition properties of isomeric families of sulfonamidopropyl-dicarba-closododecaboranes group(s) prepared using an ew direct fivestep synthesis from the correspondingp arent cages. The protocol offers ar eliable solutionf or synthesis of singly and doubly substituted dicarba-closo-dodecaboranes with ad ifferent geometric positiono fc arbon atoms. The closo-compounds from the ortho-and meta-series were then degraded to corresponding 11-vertex dicarba-nido-undecaborate(1À) anions. All compounds show in vitro enzymatic activity against CA IX in the low nanomolar or subnanomolar range. This is accompanied by clear isomer dependence of the inhibition constant(K i)a nd selectivity towardsC AI X. Decreasing trends in K i ands electivity index (S I)v alues are observed with increasing separation of the cage carbon atoms. Interactions of compounds with the active sites of CA IX were explored with X-ray crystallography,a nd eight high-resolution crystal structures uncovered the structuralb asis of inhibition potencya nd selectivity.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Direct Introduction of an Alkylsulfonamido Group on C‐sites of Isomeric Dicarba‐closo‐dodecaboranes: The Influence of Stereochemistry on Inhibitory Activity against the Cancer‐Associated Carbonic Anhydrase IX Isoenzyme

Nekvinda

Kugler

Holub

et al. 2020

Chemistry A European J

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“…Materials and Instrumentation. EtSCN was purchased from Aldrich, whereas n PrSCN was prepared in accord with the published method, 44 but using propyl bromide instead of propyl iodide. Solvents were obtained from commercial sources and used as received.…”

Section: Methodsmentioning

confidence: 99%

Recognition of S···Cl Chalcogen Bonding in Metal-Bound Alkylthiocyanates

Yandanova

Ivanov

Kuznetsov

et al. 2016

Crystal Growth & Design

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Reaction of K2[PtCl4] with excess AlkSCN in water gives the alkylthiocyanate complexes trans-[PtCl2(AlkSCN)2] (Alk = Et 1, n Pr 2; 80–85%). These species were studied, in particular, by X-ray crystallography. In the solid state, both 1 and 2 exhibit the previously unreported S···Cl chalcogen bonding, which consolidates the complexes into networks and leads to layered structures. Theoretical density functional theory calculations and Bader’s atoms in molecules analysis demonstrated two types of intermolecular interactions in tetramer (1)4, viz. the S···Cl chalcogen and the H···Cl hydrogen bonds. Despite that each particular S···Cl or H···Cl bonding is weak with the estimated energy of 1–2 kcal/mol, altogether they play a crucial role in the stabilization of the S2Cl2 fragment in (1)4, the basis set of superposition error corrected interaction energy being −12.8 kcal/mol per monomer complex molecule. The chalcogen bonding and the rhomboidal structure of the S2Cl2 fragment can be interpreted in terms of electrostatic arguments as a result of the interaction between the belt of negative electrostatic potential around the Cl atoms and the sulfur σ-holes. The natural bond orbital analysis revealed that both LP(S) → LP*(Pt)/σ*(Pt–N)/σ*(Pt–Cl) and LP(Cl) → σ*(S–C) types of hyperconjugative charge transfers are important in the chalcogen bonding.

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“…Among the organosulfur compounds, thiocyanates are ubiquitous motifs in bioactive compounds due to their stability and promising physiochemical properties . They also serve as valuable intermediates in the synthesis of diverse organosulfur compounds such as thioethers, thiols, thiotetrazoles, trifluoromethyl sulfides, disulfides, thiocarbamates, alkynyl thioethers, sulfonyl chlorides, etc. Hence, numerous methods have been developed for the synthesis of alkyl, aryl, and vinyl thiocyanates .…”

Section: Introductionmentioning

confidence: 99%

Expeditious Access to Spiro-Fused 2,5-Cyclohexadienones via Thio(seleno)cyanative ipso-Cyclization

2020

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A facile oxidative dearomatization of N-(pmethoxyaryl)propiolamides has been established for the synthesis of spiro-fused 2,5-cyclohexadienone frameworks via thio(seleno)cyanative ipso-cyclization in the presence of ceric ammonium nitrate (CAN) as the oxidant. The present method, involving the formation of C−S and C−C bonds, was also extended to (pmethoxyaryl)propiolates for thiocyanative ipso-cyclization. Furthermore, the obtained chalcogeno-spirocyclohexadienones were transformed into uniquely functionalized spirocyclohexadienone derivatives.

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A new synthesis of alkane and polyfluoroalkanesulfonyl chlorides

Abstract: This study describes a new and advantageous procedure for the synthesis of alkanesulfonyl chlorides (2) by the reaction of alkyl thiocyanates (1) with sulfuryl chloride in a mixture of acetic acid and water. The alkanesulfonyl chlorideswere obtained in good yields.

Cited by 6 publications

References 16 publications

Direct Introduction of an Alkylsulfonamido Group on C‐sites of Isomeric Dicarba‐closo‐dodecaboranes: The Influence of Stereochemistry on Inhibitory Activity against the Cancer‐Associated Carbonic Anhydrase IX Isoenzyme

Direct Introduction of an Alkylsulfonamido Group on C‐sites of Isomeric Dicarba‐closo‐dodecaboranes: The Influence of Stereochemistry on Inhibitory Activity against the Cancer‐Associated Carbonic Anhydrase IX Isoenzyme

Recognition of S···Cl Chalcogen Bonding in Metal-Bound Alkylthiocyanates

Expeditious Access to Spiro-Fused 2,5-Cyclohexadienones via Thio(seleno)cyanative ipso-Cyclization

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