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Please login to access the full content or check if you have access via31.1.1.5.2.5 Variation 5: Reaction with Nitrosonium Tetrafluoroborate
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Sandford, G., Science of Synthesis, (2007) 31, 64.
A useful variation on the Balz–Schiemann reaction (see Section 31.1.1.5.2.3) involves the use of commercially available nitrosonium tetrafluoroborate, which acts as both the diazotizing and the fluorinating agent.[154] The nonacidic conditions of this process facilitate the fluorination of aromatic amines 60 bearing acid-sensitive functional groups, such as ester, aldehyde, or N-acetyl substituents (Scheme 33). However, the relatively high cost of the nitrosonium tetrafluoroborate probably limits the use of this method to small-scale syntheses of fluoroarenes 61.
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Me8 | Meeee (%) | Mee |
---|---|---|
Me | 88 | [888] |
8-MeM8M8 | 88 | [888] |
8-MeM8M8 | 88 | [888] |
8-MM8M8 | 88 | [888] |
8-Mee | 88 | [888] |
8-MMM8M8 | 88 | [888] |
8-MeMM8M8 | 88 | [888] |
8-MeM8M8 | 88 | [888] |
8-MMMM8M8 | 88 | [888] |
8-(MeM8MMM8)M8M8 | 88 | [888] |
8-MeM8MM8M8 | 88 | [888] |
8-(MM8MMM8)M8M8 | 88 | [888] |
8-MM8MM8M8 | 88 | [888] |
8-MM8MM8M8 | 88 | [888] |
8-Me-8-MM8MM8M8 | 88 | [888] |
8-MeMMM8M8 | 88 | [888] |
8-M8MM8M8 | 88 | [888] |
8-M8MM8M8 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeee 88; Meeeeee Meeeeeeee:[888]
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References
[154] | Meeeee, M. M., Meeee. Meeeee., (8888) 88, 88. |
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