4-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate → Phenylsulfur Pentafluoride

HRID 926089Notes

Reaction equation

HRID 926089 reaction equation
F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+]#N)=[CH:10][CH:9]=1>CO>[C:8]1([S:7]([F:19])([F:6])([F:16])([F:17])[F:18])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 9942464Phenylsulfur Pentafluoride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diazonium salt 1 reacted slowly in MeOH at room temperature to give Ph-SF5 as a major product along with p-SF5—C6H4OH and p-SF5—C6H4OMe as minor products. The rate of dediazoniation was found to increase in warm MeOH; the reaction was nearly complete after 90 min. The observed product distribution, seen in FIG. 9, is consistent with homolytic dediazoniation as the predominant mechanistic pathway (Zollinger, in: Diazo Chemistry I, VCH Verlagsgesellschaft, Weinheim, Germany, 1994, chapter 8).

Sources & evidence

ORD record
ord-f9e5065b13a543c593e7e317083fce62
Source dataset
uspto-grants-2016_03
Patent number
US09284336B1

Reaction notes

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