Home / Publications / Unexpected spontaneous ring-contraction rearrangement of trifluoromethylated 1,2-oxazine N-oxides to 1-pyrroline N-oxides

Unexpected spontaneous ring-contraction rearrangement of trifluoromethylated 1,2-oxazine N-oxides to 1-pyrroline N-oxides

Vladislav Yurievich Korotaev 1
Vladislav Yurievich Korotaev
Alexey Yurievich Barkov 1
Alexey Yurievich Barkov
Pavel Alexandrovich Slepukhin 2
Pavel Alexandrovich Slepukhin
Mikhail Isaakovich Kodess 2
Mikhail Isaakovich Kodess
Vyacheslav Yakovlevich Sosnovskikh
Published 2011-09-14
CommunicationVolume 21, Issue 5, 277-279
11
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Korotaev V. Y. et al. Unexpected spontaneous ring-contraction rearrangement of trifluoromethylated 1,2-oxazine N-oxides to 1-pyrroline N-oxides // Mendeleev Communications. 2011. Vol. 21. No. 5. pp. 277-279.
GOST all authors (up to 50) Copy
Korotaev V. Y., Barkov A. Y., Slepukhin P. A., Kodess M. I., Sosnovskikh V. Y. Unexpected spontaneous ring-contraction rearrangement of trifluoromethylated 1,2-oxazine N-oxides to 1-pyrroline N-oxides // Mendeleev Communications. 2011. Vol. 21. No. 5. pp. 277-279.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2011.09.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.016
TI - Unexpected spontaneous ring-contraction rearrangement of trifluoromethylated 1,2-oxazine N-oxides to 1-pyrroline N-oxides
T2 - Mendeleev Communications
AU - Korotaev, Vladislav Yurievich
AU - Barkov, Alexey Yurievich
AU - Slepukhin, Pavel Alexandrovich
AU - Kodess, Mikhail Isaakovich
AU - Sosnovskikh, Vyacheslav Yakovlevich
PY - 2011
DA - 2011/09/14
PB - Mendeleev Communications
SP - 277-279
IS - 5
VL - 21
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2011_Korotaev,
author = {Vladislav Yurievich Korotaev and Alexey Yurievich Barkov and Pavel Alexandrovich Slepukhin and Mikhail Isaakovich Kodess and Vyacheslav Yakovlevich Sosnovskikh},
title = {Unexpected spontaneous ring-contraction rearrangement of trifluoromethylated 1,2-oxazine N-oxides to 1-pyrroline N-oxides},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.016},
number = {5},
pages = {277--279},
doi = {10.1016/j.mencom.2011.09.016}
}
MLA
Cite this
MLA Copy
Korotaev, Vladislav Yurievich, et al. “Unexpected spontaneous ring-contraction rearrangement of trifluoromethylated 1,2-oxazine N-oxides to 1-pyrroline N-oxides.” Mendeleev Communications, vol. 21, no. 5, Sep. 2011, pp. 277-279. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.016.

Abstract

6-Amino-4-trifluoromethyl-5,6-dihydro-4H-1,2-oxazine 2-oxides undergo spontaneous rearrangement into 4-amino-2-hydroxy-4-trifluoromethyl-3,4-dihydro-2H-pyrrole 1-oxides.

References

1.
10.1016/j.mencom.2011.09.016_bib0005_1
Ono
The Nitro Group in Organic Synthesis, 2001
2.
Oxoalkylation of carbonyl compounds with conjugated nitro olefins
Yoshikoshi A., Miyashita M.
Accounts of Chemical Research, 1985
5.
Reaction of Enamines with Nitro Olefins1
Kuehne M.E., Foley L.
Journal of Organic Chemistry, 1965
6.
Enamine Chemistry. IV. Cycloaddition Reactions of Enamines Derived from Aldehydes and Acyclic Ketones1,2
Brannock K.C., Bell A., Burpitt R.D., Kelly C.A.
Journal of Organic Chemistry, 1964
10.
α-Nitrostyrene. First reactions with enamines
Bradamante P., Pitacco G., Risaliti A., Valentin E.
Tetrahedron Letters, 1982
11.
10.1016/j.mencom.2011.09.016_bib0015_7
Benedetti
ARKIVOC, 2001
13.
1-nitro-1-phenylpropene
Asaro F., Pitacco G., Valentin E.
Tetrahedron, 1987
14.
Mononitroalkylations of Butane-2,3-dione
Pitacco G., Pizzioli A., Valentin E.
Synthesis, 1996
16.
10.1002/(SICI)1522-2675(19991110)82:11<1829::AID-HLCA1829>3.0.CO;2-#
18.
New C−C Coupling Reaction of Cyclic Nitronates with Carbon Nucleophiles. Umpolung of the Conventional Reactivity of Nitronates
Smirnov V.O., Ioffe S.L., Tishkov A.A., Khomutova Y.A., Nesterov I.D., Antipin M.Y., Smit W.A., Tartakovsky V.A.
Journal of Organic Chemistry, 2004
19.
10.1016/j.mencom.2011.09.016_bib0025_3
Klenov
Synthesis, 2004
20.
Ring-contraction reactions of bicyclic nitronic esters
Barbarella G., Pitacco G., Russo C., Valentin E.
Tetrahedron Letters, 1983
21.
Cyclopentaannulation reactions between nitrocycloalkenes and diacetyl morpholino enamine
Felluga F., Nardin G., Nitti P., Pltacco G., Valentin E.
Tetrahedron, 1988
22.
[3 + 2] Carbocyclization reactions of linear α-ketoenamines with conjugated nitroolefins
Felluga F., Nitti P., Pitacco G., Valentin E.
Journal of the Chemical Society Perkin Transactions 1, 1991
23.
Notes- Diels-Alder Diene Synthesis with 1,1,1-Trichloro-3-nitropropene
Burkett H., Wright W.
Journal of Organic Chemistry, 1960
25.
10.1016/j.mencom.2011.09.016_bib0045_1
Barański
Pol. J. Chem., 1982
26.
Trifluoropropenes as Dipolarophiles.
Tanaka K., Mori T., Mitsuhashi K.
Bulletin of the Chemical Society of Japan, 1993
28.
10.1016/j.mencom.2011.09.016_bib0045_4
Jasiński
Pol. J. Chem., 2006
29.
Korotaev V.Y., Sosnovskikh V.Y., Barabanov M.A., Barkov A.Y., Kodess M.I.
Mendeleev Communications, 2010
30.
1,1,1-Trichloro-2-arylamino-3-nitropropanes
Brower F., Burkett H.
Journal of the American Chemical Society, 1953
31.
Heterocyclic Compounds via 1,1,1-Trichloro-3-nitropropene and 1,1,1-Trichloro-3-aminopropanol-21
Burkett H., Nelson G., Wright W.
Journal of the American Chemical Society, 1958
32.
3,3,3-Trifluoro-1-nitropropene as a Novel Trifluoromethyl-Containing Building Block
Iwata S., Ishiguro Y., Utsugi M., Mitsuhashi K., Tanaka K.
Bulletin of the Chemical Society of Japan, 1993
35.
10.1016/j.mencom.2011.09.016_bib0060
Aizikovich
Zh. Org. Khim., 1998
36.
New functionalized, differently fluorinated building-blocks via Michael addition to γ-fluoro-α-nitroalkenes
Molteni M., Consonni R., Giovenzana T., Malpezzi L., Zanda M.
Journal of Fluorine Chemistry, 2006
37.
Korotaev V.Y., Barkov A.Y., Slepukhin P.A., Kodess M.I., Sosnovskikh V.Y.
Mendeleev Communications, 2011
38.
The Ethanolysis of 1,1,1-Trifluoro-2,3-epoxybutane and 2-Methyl-1,1,1-trifluoro-2,3-epoxypropane
McBee E.T., Hathaway C.E., Roberts C.W.
Journal of the American Chemical Society, 1956
39.
Ψ[CH(CF3)NH]Gly-peptides: synthesis and conformation analysis
Molteni M., Bellucci M.C., Bigotti S., Mazzini S., Volonterio A., Zanda M.
Organic and Biomolecular Chemistry, 2009
40.
10.1016/j.mencom.2011.09.016_bib0075_3
Korotaev
Izv. Akad. Nauk, Ser. Khim., 2009
41.
Correlation of the Base Strengths of Amines1
Hall H.K.
Journal of the American Chemical Society, 1957
43.
Tautomeric Equilibria in Relation to Pi-Electron Delocalization
Raczyńska E.D., Kosińska W., Ośmiałowski B., Gawinecki R.
Chemical Reviews, 2005
44.
Ring-closure reactions of alkenyl oximes induced by persulfate anion oxidation of diphenyl diselenide. Formation of 1,2-oxazines and cyclic nitrones
Tiecco M., Testaferri L., Tingoli M., Bagnoli L., Marini F.
Journal of the Chemical Society Perkin Transactions 1, 1993
45.
Alkylation of enamines by α-haloketoximes
Bravo P., Gaudiano G., Ponti P.P., Umani-Ronchi A.
Tetrahedron, 1970
46.
Preparation of 1,1,1-Trichloro-3-nitro-2-alkenes1
BACHMAN G.B., STANDISH N.W.
Journal of Organic Chemistry, 1961
49.
10.1016/j.mencom.2011.09.016_bib0100_4
Colonge
Bull. Soc. Chim. Fr., 1964
50.
Cyclic nitronic esters
Nielsen A.T., Archibald T.G.
Tetrahedron, 1970
52.
10.1016/j.mencom.2011.09.016_bib0105_3
Smirnov
Izv. Akad. Nauk, Ser. Khim., 2006
53.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007