2007
DOI: 10.1002/chin.200709066
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A Convenient and Efficient Method for Incorporation of Pentafluorosulfanyl (SF5) Substituents into Aliphatic Compounds.

Abstract: Thio compounds P 0440A Convenient and Efficient Method for Incorporation of Pentafluorosulfanyl (SF 5 ) Substituents into Aliphatic Compounds. -SF 5 Cl as well as SF 5 Br smoothly undergo efficient addition to a variety of alkenes and alkynes under mild, free radical chain reaction conditions. The SF5Cl addition reactions are regiospecific, highly diastereoselective and relatively insensitive to a wide range of non-allylic functionalities.-(DOLBIER*, W. R. J.; AIT-MOHAND, S.; SCHERTZ, T. D.; SERGEEVA, T. A.; C… Show more

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Cited by 2 publications
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“…The pentafluorosulfanyl (-SF 5 ) functional group is of recent interest (a) because of its similarity to and differences from the trifluoromethyl (-CF 3 ) group, (b) because of its potential use in biochemically active substances, 11 and (c) because of new synthetic techniques for introducing the group to organic molecules. 12 Because there are relatively few known materials containing the pentafluorosulfanyl group, its effects on the physical properties of substances containing it are relatively unknown. The trifluoromethyl group is present in many more known materials, and it would be useful to understand the properties of the SF 5 -containing compounds based on knowledge of the properties of the CF 3 -containing compounds.…”
Section: Normal Boiling Temperaturesmentioning
confidence: 99%
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“…The pentafluorosulfanyl (-SF 5 ) functional group is of recent interest (a) because of its similarity to and differences from the trifluoromethyl (-CF 3 ) group, (b) because of its potential use in biochemically active substances, 11 and (c) because of new synthetic techniques for introducing the group to organic molecules. 12 Because there are relatively few known materials containing the pentafluorosulfanyl group, its effects on the physical properties of substances containing it are relatively unknown. The trifluoromethyl group is present in many more known materials, and it would be useful to understand the properties of the SF 5 -containing compounds based on knowledge of the properties of the CF 3 -containing compounds.…”
Section: Normal Boiling Temperaturesmentioning
confidence: 99%
“…While we have found simple or linear relationships for a wide variety of other properties and a wide variety of families of materials, we here show just one more example. The pentafluorosulfanyl (−SF 5 ) functional group is of recent interest (a) because of its similarity to and differences from the trifluoromethyl (−CF 3 ) group, (b) because of its potential use in biochemically active substances, and (c) because of new synthetic techniques for introducing the group to organic molecules . Because there are relatively few known materials containing the pentafluorosulfanyl group, its effects on the physical properties of substances containing it are relatively unknown.…”
Section: Normal Boiling Temperaturesmentioning
confidence: 99%
“…The synthesis of alkyl and alkenyl SF 5 compounds via pentafluorosulfanylation of their alkenyl and alkynyl, respectively, precursors is largely based on the Dolbier method. 3…”
Section: Methods For Incorporation/manipulation Of Sf 4 ...mentioning
confidence: 99%
“…α-SF 5 ketones represent valuable building blocks for further chemical diversifications and applications, but, despite their potential usefulness, only few examples were reported until 2017. 34a b With the aim of establishing if the SF 5 group could efficiently direct the addition of water to a neighboring alkyne, Paquin et al described the first regioselective gold-catalyzed hydration of SF 5 -alkynes. 34c The latter were synthesized from the corresponding alkynes using the Dolbier’s protocol, followed by a base-promoted elimination.…”
Section: Synthesis Of Sf 5 /Sf 4 Cl/s...mentioning
confidence: 99%
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