Journal
ORGANIC LETTERS
Volume 16, Issue 2, Pages 596-599Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol403495e
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Funding
- National Science and Engineering Research Council of Canada (NSERC)
- Fonds Quebecois de Recherche - Nature et Technologies (FQRNT)
- Canada Foundation for Innovation (CFI)
- Centre in Green Chemistry and Catalysis (CGCC)
- Universite de Sherbrooke
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Even after more than 50 years since its discovery, the electrophilic potential of diazirines was never truly exploited. This longstanding limitation has been resolved. N-Monosubstituted diaziridines and hydrazones are obtained by nucleophilic additions. They release, under hydrolysis conditions, the corresponding monosubstituted hydrazines. The latter were converted to pyrazoles in high yields. The adamantanone can be recovered in 80-100% yields. This work demonstrates the potential of diazirines as electrophilic nitrogen sources with recoverable protecting groups.
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