Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds

Filip SV, Sewald N (2005)
SYNTHESIS-STUTTGART 2005(20): 3565-3570.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
The reaction of alpha-chloronitrosocyclohexane with allyl-zinc reagents in THF selectively provides O-allylcyclohexanone oximes in very good yields in an ene type reaction followed by zinc halide elimination. N-Allyl hydroxylalnines are formed as m inor products via N-allyl nitrones when a nonpolar solvent, e.g. toluene, is employed. In both cases complete allylic transposition with respect to the allylic organozinc reagent is observed. Compared to non-metalated allyl compounds, which give N-allyl nitrones upon reaction with alpha-chloronitroso compounds, the use of zinc as hydrogen equivalent in an ene type reaction displays a drastic change of reactivity.
Stichworte
ene reactions; zinc; allylations; reagents; organometallic; regioselectivity
Erscheinungsjahr
2005
Zeitschriftentitel
SYNTHESIS-STUTTGART
Band
2005
Ausgabe
20
Seite(n)
3565-3570
ISSN
0039-7881
eISSN
1437-210X
Page URI
https://pub.uni-bielefeld.de/record/1600909

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Filip SV, Sewald N. Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds. SYNTHESIS-STUTTGART. 2005;2005(20):3565-3570.
Filip, S. V., & Sewald, N. (2005). Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds. SYNTHESIS-STUTTGART, 2005(20), 3565-3570. doi:10.1055/s-2005-918429
Filip, S. V., and Sewald, N. (2005). Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds. SYNTHESIS-STUTTGART 2005, 3565-3570.
Filip, S.V., & Sewald, N., 2005. Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds. SYNTHESIS-STUTTGART, 2005(20), p 3565-3570.
S.V. Filip and N. Sewald, “Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds”, SYNTHESIS-STUTTGART, vol. 2005, 2005, pp. 3565-3570.
Filip, S.V., Sewald, N.: Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds. SYNTHESIS-STUTTGART. 2005, 3565-3570 (2005).
Filip, SV, and Sewald, Norbert. “Formation of O-allyl oximes by reaction of allylzinc reagents with alpha-chloronitroso compounds”. SYNTHESIS-STUTTGART 2005.20 (2005): 3565-3570.