TY - JOUR
T1 - Diethyl chlorophosphite
T2 - A versatile reagent
AU - Jie, Zhou
AU - Rammoorty, Vebumani
AU - Fischer, Bilha
PY - 2002/2/8
Y1 - 2002/2/8
N2 - Diethyl chlorophosphite (DECP) was previously described as a reducing agent for nitro compounds to the corresponding amines (Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393). Here, the utility of this reagent was extended to chemical conversions of other oxygenated functional groups. In this paper we report on the scope of the reaction of DECP with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes. The chemoselectivity of DECP is described, and conditions for a stepwise multiple conversion of functional groups on the same molecule with this reagent are provided.
AB - Diethyl chlorophosphite (DECP) was previously described as a reducing agent for nitro compounds to the corresponding amines (Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393). Here, the utility of this reagent was extended to chemical conversions of other oxygenated functional groups. In this paper we report on the scope of the reaction of DECP with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes. The chemoselectivity of DECP is described, and conditions for a stepwise multiple conversion of functional groups on the same molecule with this reagent are provided.
UR - http://www.scopus.com/inward/record.url?scp=0037039884&partnerID=8YFLogxK
U2 - 10.1021/jo0106851
DO - 10.1021/jo0106851
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
C2 - 11856010
AN - SCOPUS:0037039884
SN - 0022-3263
VL - 67
SP - 711
EP - 719
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -