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Synthesis, Structure and Facile Rearrangement of a (Bromomethylene)-cyclopropane–Dichloroketene Adduct

Nadezhda Alexsandrovna Donskaya 1
Nadezhda Alexsandrovna Donskaya
, 
Boris Aleksandrovich Lukovskii 1
Boris Aleksandrovich Lukovskii
10.1070/MC1991v001n04ABEH000078
Published 1991-12-31
Communication , Volume 1, Issue 4, 127-128
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Donskaya N. A., Lukovskii B. A. Synthesis, Structure and Facile Rearrangement of a (Bromomethylene)-cyclopropane–Dichloroketene Adduct // Mendeleev Communications. 1991. Vol. 1. No. 4. pp. 127-128.
GOST all authors (up to 50) Copy
Donskaya N. A., Lukovskii B. A. Synthesis, Structure and Facile Rearrangement of a (Bromomethylene)-cyclopropane–Dichloroketene Adduct // Mendeleev Communications. 1991. Vol. 1. No. 4. pp. 127-128.
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TY - JOUR
DO - 10.1070/MC1991v001n04ABEH000078
UR - https://mendcomm.colab.ws/publications/10.1070/MC1991v001n04ABEH000078
TI - Synthesis, Structure and Facile Rearrangement of a (Bromomethylene)-cyclopropane–Dichloroketene Adduct
T2 - Mendeleev Communications
AU - Donskaya, Nadezhda Alexsandrovna
AU - Lukovskii, Boris Aleksandrovich
PY - 1991
DA - 1991/12/31
PB - Mendeleev Communications
SP - 127-128
IS - 4
VL - 1
ER -
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@article{1991_Donskaya,
author = {Nadezhda Alexsandrovna Donskaya and Boris Aleksandrovich Lukovskii},
title = {Synthesis, Structure and Facile Rearrangement of a (Bromomethylene)-cyclopropane–Dichloroketene Adduct},
journal = {Mendeleev Communications},
year = {1991},
volume = {1},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1991v001n04ABEH000078},
number = {4},
pages = {127--128},
doi = {10.1070/MC1991v001n04ABEH000078}
}
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Donskaya, Nadezhda Alexsandrovna, and Boris Aleksandrovich Lukovskii. “Synthesis, Structure and Facile Rearrangement of a (Bromomethylene)-cyclopropane–Dichloroketene Adduct.” Mendeleev Communications, vol. 1, no. 4, Dec. 1991, pp. 127-128. https://mendcomm.colab.ws/publications/10.1070/MC1991v001n04ABEH000078.

Abstract

5,5-Dichloro-6-bromospiro[2.3]hexan-4-one 2 is produced by the reaction of (bromomethylene)cyclopropane 1 with dichloroketene and rearranges readily at 0°C into 2-(2-bromoethyl)-4,4-dichlorocyclobut-2-enone 4a; reaction of 2 with basic reagents leads to the formation of 1-vinylcyclopropanecarboxylic acid derivatives.

References

1.
N A. Donskaya, A. G. Bessmertnykh, B. A. Lukovskii, M. Yu. Kisina and M. A. Ryabova, Zh. Org. Khim., in the press.
2.
Vinyl cations. 14. Preparation and solvolysis of (bromomethylene)cyclopropanes. Generation of stabilized vinyl cations
Hanack M., Baessler T., Eymann W., Heyd W.E., Kopp R.
Journal of the American Chemical Society, 1974
6.
10.1070/MC1991v001n04ABEH000078_bib6
Bessmertnykh
Zh. Org. Khim., 1991
7.
10.1070/MC1991v001n04ABEH000078_bib7
Dolgii
Izv. Akad. Nauk SSSR, Ser. Khim., 1980