Intermolecular electrophilic O-amination of alcohols.
We report the first examples of an intermolecular electrophilic O-amination of aliphatic alcohols. Thus, the new reagents, fluorenone oxime tosylate, 5a, or mesylate, 5b, permit O-amination of diverse alcohols in the presence of NaH under mild conditions. By following the formation of the resulting oxime ethers, 6, the reaction was shown to be sensitive to steric effects in the alcohol. Furthermore, the presence of an aromatic ring or of a double bond in the alcohol molecule (benzyl, allyl) was found to increase the reaction rate.
Hassner
Alfred
A
Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. hassna@mail.biu.ac.il
Patchornik
Guy
G
Pradhan
Tarun K
TK
Kumareswaran
R
R
D000438:Alcohols / Q000737:chemistry*; D000586:Amination; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D004987:Ethers; D010091:Oximes