Exploratory study of the reaction of bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor™ reagent) with diaryl sulfoxides: novel routes to Ar2SF2 and Ar2SF(OTf) via sulfoxide activation
摘要:
Neither bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor(TM) reagent) nor HF/pyridine alone can fluorinate diaryl sulfoxides. S-fluorination can be effected by activating the sulfoxide via protonation with HF/pyridine (70:30) to form sulfoxonium ions in equilibrium which are then S-fluorinated in situ with Deoxofluor(TM) to give Ar2SF2 compounds. Conversions depend strongly on steric factors and the reactions require the use of excess Deoxofluor(TM) and HF/pyridine. NMR data for the resulting diarylsulfur difluorides are gathered and discussed. Sulfoxide activation via diaryl (trifloxy) sulfonium. triflate generated in situ from Ar2SO with triflic anhydride at low temperature represents another strategy for S-fluorination with Deoxofluor(TM) to generate Ar2S(OTf)F. (C) 2002 Elsevier Science B.V. All rights reserved.
The synthesis and mechanism of formation of cis- and trans-Ph2SF4 is described. Starting compounds are Ph2S or Ph2SF2 and the oxidizing agent is XeF2 in the presence of Et4NCl. Also described is the synthesis of related chalcogen(IV and VI) fluorides such as t-butylSF3, difluorodibenzothiophene, PhSeF3, Ph2SeF2, PhSF5, p-MeC6H4SF5, PhSeF5, and PhTeF5. The reactions of Ph2S(O)F2 with alcohols and with
描述了顺-和反-Ph 2 SF 4的合成及其形成机理。在Et 4 NCl存在下,起始化合物为Ph 2 S或Ph 2 SF 2,氧化剂为XeF 2。还描述了相关的硫族元素的合成(IV和VI)氟化物,如吨-butylSF 3,difluorodibenzothiophene,PhSEF 3中,Ph 2 SEF 2,PHSF 5,p -MeC 6 ħ 4 SF 5,PhSEF 5和PhTeF 5。简要介绍了Ph 2 S(O)F 2与醇和H 2 O-HF玻璃系统的反应。
Ruppert,I., Chemische Berichte, 1979, vol. 112, p. 3023 - 3030
作者:Ruppert,I.
DOI:——
日期:——
Tetrafluorothiirane
作者:W. R. Brasen、H. N. Cripps、C. G. Bottomley、M. W. Farlow、C. G. Krespan
DOI:10.1021/jo01023a048
日期:1965.12
RUPPERT I., CHEM. BER., 1979, 112, NO 8, 3023-3030