N‐alkyl‐C‐polyfluoroalkyl‐C‐chlorosulfinimides R<sub>F</sub>C(Cl)SNR

Ahlemann, Jens-Thomas; Roesky, Herbert W.; Markovsky, L. N.; Тимошенко, Вадим М.; Shermolovich, Yuri G.

doi:10.1002/hc.520060105

Cited by 7 publications

(1 citation statement)

References 12 publications

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“…At dehydrochlorination of these compounds by lithium hexamethyldisilazide formed thermally stable C-Cl-sulfinimides R F C(Cl)=S=NR [6,7]. At dehydrochlorination of these compounds by lithium hexamethyldisilazide formed thermally stable C-Cl-sulfinimides R F C(Cl)=S=NR [6,7].…”

mentioning

confidence: 99%

1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

et al. 2005

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mentioning

confidence: 99%

1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

et al. 2005

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ChemInform Abstract: N‐Alkyl‐C‐polyfluoroalkyl‐C‐chlorosulfinimides RFC(Cl)=S=N‐R.

et al. 1995

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5‐Chloro‐5‐trifluoromethyl‐3‐aryl‐4‐alkyl(aryl)‐isothiazolidines and their Dehydrochlorination Reactions

Solov'ev

Chernega

Almsick

et al. 2005

Zeitschrift anorg allge chemie

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N-Alkyl(aryl)-C-trifluoromethyl-C-chlorosulfinimides and styrenes react to give the 3ϩ2 cycloaddition products, 5chloro-5-trifluoromethyl-3-aryl-4-alkyl(aryl)-isothiazolidines 9a-h. The structure of the dehydrochlorination products derived from the compounds 9a-h is determined by the nature of the substituent near the nitrogen atom. The compounds having bulky tertiary-butyl group (9c,h) are transformed into the isothiazolines derivatives 10a,b, but compounds 9a,b,d-g form β-aminovinyl trifluoromethylthioketones 11a-f.The nature of the substituent near the nitrogen atom in the molecule 9 influences not only the thermal stability of the isothiazolidines but also their transformations during dehydrochlorination.Compounds 9c,h with a tertiary-butyl substituent near the nitrogen atom form isothiazolidines 10a,b upon heating with triethylamine in toluene. All the other isothiazolidine derivatives 9a,b,d-g are transformed into b-aminovinylthioketones 11a-f under the same conditions, meaning that hydrogen chloride elimination is accompanied by isothiazoline cycle opening.Examples of the isothiazoline cycle S-N bond rupture upon attack of nucleophilic reagents on the sulfur atom are known in the literature [12]. It may be assumed that the difference in the dehydrochlorination results for compounds 9 is caused by the shielding effect of the tertiary-butyl substituent, which prevents the attack on the sulfur atom in isothiazolines 10a,b by chloride ion. In contrast to this, the attack is possible in the isothiazolines 12, intermediately formed by dehydrochlorination of the compounds 9a,b,d-g. This attack results in the rupture of the sulfur-nitrogen bond and formation of thioketones 11a-f.Fluorine-containing thioketones 11c,e are red crystalline compounds and thioketones 11a,b,d,f are viscous red liquids which were purified by chromatography on silicagel. The first thioketones of this type were obtained as a result of β-aminovinylketones thionation [13].An apparently anomalous low-field chemical shift in the 1 H NMR spectra for the proton connected to nitrogen of compounds 11a-f (ϳ15 ppm) is noteworthy (see experimental part and [13]). The investigation of the structure of compound 11e by single-crystal X-ray diffraction allowed us to determine the reason of such a low-field δ NH value.

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N‐alkyl‐C‐polyfluoroalkyl‐C‐chlorosulfinimides R_FC(Cl)SNR

Abstract: The N-alkyl-C-polyfluoroalkyl-C-chlorosulfnimides R,C(Cl) =S=N-R have been investigated. Some aspects of their thermal stability and their [3+2] and [3+ 13 cycloaddition reactions have been examined. Q 1995 VCH Publishers, Inc.

Cited by 7 publications

References 12 publications

1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

ChemInform Abstract: N‐Alkyl‐C‐polyfluoroalkyl‐C‐chlorosulfinimides RFC(Cl)=S=N‐R.

5‐Chloro‐5‐trifluoromethyl‐3‐aryl‐4‐alkyl(aryl)‐isothiazolidines and their Dehydrochlorination Reactions

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N‐alkyl‐C‐polyfluoroalkyl‐C‐chlorosulfinimides RFC(Cl)SNR

Abstract: The N-alkyl-C-polyfluoroalkyl-C-chlorosulfnimides R,C(Cl) =S=N-R have been investigated. Some aspects of their thermal stability and their [3+2] and [3+ 13 cycloaddition reactions have been examined. Q 1995 VCH Publishers, Inc.

Cited by 7 publications

References 12 publications

1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

1,1-Dichloropolyfluoroalkanesulfenamides and Their Dehydrochlorination Effected by Triethylamine

ChemInform Abstract: N‐Alkyl‐C‐polyfluoroalkyl‐C‐chlorosulfinimides RFC(Cl)=S=N‐R.

5‐Chloro‐5‐trifluoromethyl‐3‐aryl‐4‐alkyl(aryl)‐isothiazolidines and their Dehydrochlorination Reactions

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N‐alkyl‐C‐polyfluoroalkyl‐C‐chlorosulfinimides R_FC(Cl)SNR