2011 Fiscal Year Final Research Report
Development of Unprecedented Hofmann Rearrangement of Sulfonamides
| Project/Area Number |
23659008
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | The University of Tokushima |
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Principal Investigator |
OCHIAI Masahito 徳島大学, 大学院・ヘルスバイオサイエンス研究部, 教授 (50127065)
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| Project Period (FY) |
2011
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| Keywords | 有機化学 |
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| Research Abstract |
We have developed the first example of Hofmann rearrangement of primary arenesulfonamides, which relies on the use of difluorobromane and affords N-arylsulfamoyl fluorides selectively. Reaction of the difluorobromane with p-toluenesulfonamide in benzene produced sulfamoyl fluoride in a high yield, through Hofmann rearrangement. Arenesulfonamides with electron-donating and-withdrawing substituents efficiently undergoes Hofmann rearrangement. The structure of N-p-tolylsulfamoyl fluoride was determined by a single-crystal X-ray analysis. The results obtained from the reaction of 2, 3, 5, 6-tetramethylbenzenesulfonamide strongly suggest that generation of sulfonyl nitrene will not be involved in this rearrangement.
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