1976
DOI: 10.1021/jo00881a007
|View full text |Cite
|
Sign up to set email alerts
|

Fluorodesulfurization. A new reaction for the formation of carbon-fluorine bonds

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1

Citation Types

0
24
0

Year Published

1985
1985
2012
2012

Publication Types

Select...
3
3

Relationship

0
6

Authors

Journals

citations
Cited by 68 publications
(24 citation statements)
references
References 5 publications
0
24
0
Order By: Relevance
“…2-Aminothiols and mercapto amino acids were successfully converted into aminoalkyl fluorides and fluorinated amino acids in liquid hydrogen fluoride solution with fluoroxytrifluoromethane (CF 3 OF), chlorine, N-chlorosuccinimide (NCS), or a fluorine-helium mixture, respectively. The reaction of D-penicillamine (111) in liquid HF at À78 8C with CF 3 OF gave 3-fluoro-D-valine (112) in 94% yield, while primary amino thiols, such as cysteine (113), by reaction with the more powerful oxidizer F 2 /He gave 3-fluoroalanine (114) and a minor amount of difluoroalanine (115) [106] (Scheme 42).…”
Section: Application Of Oxidants and Nucleophilic Fluorinating Reagentsmentioning
confidence: 99%
See 2 more Smart Citations
“…2-Aminothiols and mercapto amino acids were successfully converted into aminoalkyl fluorides and fluorinated amino acids in liquid hydrogen fluoride solution with fluoroxytrifluoromethane (CF 3 OF), chlorine, N-chlorosuccinimide (NCS), or a fluorine-helium mixture, respectively. The reaction of D-penicillamine (111) in liquid HF at À78 8C with CF 3 OF gave 3-fluoro-D-valine (112) in 94% yield, while primary amino thiols, such as cysteine (113), by reaction with the more powerful oxidizer F 2 /He gave 3-fluoroalanine (114) and a minor amount of difluoroalanine (115) [106] (Scheme 42).…”
Section: Application Of Oxidants and Nucleophilic Fluorinating Reagentsmentioning
confidence: 99%
“…In due course the original hazardous combination of reagents (CF 3 OF and/or F 2 /He) [106] were replaced by more convenient reagents such as N-bromosuccinimide (NBS)/Olah's reagent (PyÁ9HF) or DAST. Nicolaou et al applied these two different methods to prepare glycosyl fluorides 117 from phenylthio glycosides 116 demonstrating the efficiency of this transformation.…”
Section: Application Of Oxidants and Nucleophilic Fluorinating Reagentsmentioning
confidence: 99%
See 1 more Smart Citation
“…The process generally is successful for replacement of thiols [1], sulfides [2], thioketals [3] and acetals [4,5], thioesters and dithioesters [6] with fluorine obtained from mixed halogens [6], mercuric fluoride [4], or diethylaminosulfur trifluoride [7]. Complete replacement of three sulfur atoms occurs only in aromatic orthothio esters [6].…”
mentioning
confidence: 99%
“…Complete replacement of three sulfur atoms occurs only in aromatic orthothio esters [6]. Aliphatic orthothioesters have received little attention, but the few known examples show either elimination without fluorination [1] or fluorination accompanied by rearrangements or oxidation [5].…”
mentioning
confidence: 99%