TY - JOUR
T1 - Intermolecular electrophilic O-amination of alcohols
AU - Hassner, Alfred
AU - Patchornik, Guy
AU - Pradhan, Tarun K.
AU - Kumareswaran, R.
PY - 2007/1/19
Y1 - 2007/1/19
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=33846228467&partnerID=8YFLogxK
U2 - 10.1021/jo061900m
DO - 10.1021/jo061900m
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C2 - 17221992
AN - SCOPUS:33846228467
SN - 0022-3263
VL - 72
SP - 658
EP - 661
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -