2006
DOI: 10.1007/s11172-006-0399-4
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Synthesis and reactivity of fluorine-containing thiols and thioacyl halides

Abstract: A route to α hydropolyfluoroalkanethiols and polyfluorothioacyl halides via thermal split ting of benzyl polyfluoroalkyl sulfides under the action of phosphorus pentoxide was proposed. The thiols obtained were used as starting materials for the synthesis of α hydropoly fluoroalkanesulfenyl chlorides. The properties of the resulting F,S containing compounds were studied.

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Cited by 15 publications
(3 citation statements)
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“…Importantly, the potential of TFE and CTFE to deplete the ozone layer is negligible . In the 1950s and 1960s, several examples of base-promoted hydrothiolation reactions of TFE and CTFE have been reported . Moreover, various organic transformations of highly functionalized organofluorine compounds have recently been realized by exploiting the unique reactivity of these fluorinated feedstock chemicals. , Previously, our group has reported the carbo-, oxy-, fluoro-, and azacupration of TFE, followed by additional functionalization reactions to synthesize tetrafluoroethyl-bridged organic compounds .…”
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confidence: 85%
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“…Importantly, the potential of TFE and CTFE to deplete the ozone layer is negligible . In the 1950s and 1960s, several examples of base-promoted hydrothiolation reactions of TFE and CTFE have been reported . Moreover, various organic transformations of highly functionalized organofluorine compounds have recently been realized by exploiting the unique reactivity of these fluorinated feedstock chemicals. , Previously, our group has reported the carbo-, oxy-, fluoro-, and azacupration of TFE, followed by additional functionalization reactions to synthesize tetrafluoroethyl-bridged organic compounds .…”
mentioning
confidence: 85%
“…We discovered that the use of polar aprotic solvents enables the hydrothiolation of various fluoroalkenes in the absence of additives to give the corresponding sulfides within 1 h . Furthermore, under the applied reaction conditions, the addition reaction occurs chemoselectively at the thiol moieties even in substrates that contain hydroxyl or amine groups that could not be used under the previous conditions involving basic additives (Scheme c) . The subsequent silylation and copper­(I)-mediated fluoroalkylation of aryl iodides also proceeds with high efficiency and substrate compatibility.…”
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confidence: 99%
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