Home / Publications / C-Alkylation of nitroso chlorides with diethyl malonate: the X-ray structure of diethyl (±)-(1R*,2S*,5R*)-2-{3(E)-hydroxyimino-2,6,6-trimethylbicyclo[3.1.1]-hept-2-yl}malonate

C-Alkylation of nitroso chlorides with diethyl malonate: the X-ray structure of diethyl (±)-(1R*,2S*,5R*)-2-{3(E)-hydroxyimino-2,6,6-trimethylbicyclo[3.1.1]-hept-2-yl}malonate

Sergey Nikolaevich Bizjaev 1
Sergey Nikolaevich Bizjaev
, 
Tatyana Valeryevna Rybalova 1
Tatyana Valeryevna Rybalova
, 
Yuriy Vasil'evich Gatilov 1
Yuriy Vasil'evich Gatilov
, 
Alexey Vasil'evich Tkachev 2
Alexey Vasil'evich Tkachev
10.1070/MC2004v014n01ABEH001799
Published 2004-03-05
Communication , Volume 14, Issue 1, 18-20
10
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Bizjaev S. N. et al. C-Alkylation of nitroso chlorides with diethyl malonate: the X-ray structure of diethyl (±)-(1R*,2S*,5R*)-2-{3(E)-hydroxyimino-2,6,6-trimethylbicyclo[3.1.1]-hept-2-yl}malonate // Mendeleev Communications. 2004. Vol. 14. No. 1. pp. 18-20.
GOST all authors (up to 50) Copy
Bizjaev S. N., Rybalova T. V., Gatilov Y. V., Tkachev A. V. C-Alkylation of nitroso chlorides with diethyl malonate: the X-ray structure of diethyl (±)-(1R*,2S*,5R*)-2-{3(E)-hydroxyimino-2,6,6-trimethylbicyclo[3.1.1]-hept-2-yl}malonate // Mendeleev Communications. 2004. Vol. 14. No. 1. pp. 18-20.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC2004v014n01ABEH001799
UR - https://mendcomm.colab.ws/publications/10.1070/MC2004v014n01ABEH001799
TI - C-Alkylation of nitroso chlorides with diethyl malonate: the X-ray structure of diethyl (±)-(1R*,2S*,5R*)-2-{3(E)-hydroxyimino-2,6,6-trimethylbicyclo[3.1.1]-hept-2-yl}malonate
T2 - Mendeleev Communications
AU - Bizjaev, Sergey Nikolaevich
AU - Rybalova, Tatyana Valeryevna
AU - Gatilov, Yuriy Vasil'evich
AU - Tkachev, Alexey Vasil'evich
PY - 2004
DA - 2004/03/05
PB - Mendeleev Communications
SP - 18-20
IS - 1
VL - 14
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2004_Bizjaev,
author = {Sergey Nikolaevich Bizjaev and Tatyana Valeryevna Rybalova and Yuriy Vasil'evich Gatilov and Alexey Vasil'evich Tkachev},
title = {C-Alkylation of nitroso chlorides with diethyl malonate: the X-ray structure of diethyl (±)-(1R*,2S*,5R*)-2-{3(E)-hydroxyimino-2,6,6-trimethylbicyclo[3.1.1]-hept-2-yl}malonate},
journal = {Mendeleev Communications},
year = {2004},
volume = {14},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2004v014n01ABEH001799},
number = {1},
pages = {18--20},
doi = {10.1070/MC2004v014n01ABEH001799}
}
MLA
Cite this
MLA Copy
Bizjaev, Sergey Nikolaevich, et al. “C-Alkylation of nitroso chlorides with diethyl malonate: the X-ray structure of diethyl (±)-(1R*,2S*,5R*)-2-{3(E)-hydroxyimino-2,6,6-trimethylbicyclo[3.1.1]-hept-2-yl}malonate.” Mendeleev Communications, vol. 14, no. 1, Mar. 2004, pp. 18-20. https://mendcomm.colab.ws/publications/10.1070/MC2004v014n01ABEH001799.

Abstract

The reactions of the nitroso chlorides of methylcyclohexene, limonene, 3-carene, and α-pinene with an excess of diethyl malonate in the presence of anhydrous K2CO3 at room temperature resulted in the C-alkylation and formation of α-substituted oximes with a diethyl malonate moiety in 20–90% yields.

References

1.
10.1070/MC2004v014n01ABEH001799_bib1
Tkachev
Ross. Khim. Zh., 1998
2.
10.1070/MC2004v014n01ABEH001799_bib2_1
Larionov
Koord. Khim., 2001
3.
10.1070/MC2004v014n01ABEH001799_bib2_2
Larionov
Koord. Khim., 2002
4.
10.1070/MC2004v014n01ABEH001799_bib2_3
Larionov
Koord. Khim., 2002
5.
Conjugated nitrosoalkenes
Lyapkalo I.M., Ioffe S.L.
Russian Chemical Reviews, 1998
6.
Stereochemistry of α-Amino Oximes From the Monoterpene Hydrocarbons Car-3-ene, Limonene and α-Pinene
Tkachev A., Rukavishnikov A., Chibiryaev A., Denisov A., Gatilov Y., Bagryanskaya I.
Australian Journal of Chemistry, 1992