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Unexpected formation of substituted naphthalenes and phenanthrenes in a GaCl3 mediated dimerization–fragmentation reaction of 2-arylcyclopropane-1,1-dicarboxylates

Roman Aleksandrovich Novikov 1
Roman Aleksandrovich Novikov
, 
Anna Vadimovna Tarasova 1
Anna Vadimovna Tarasova
, 
Kirill Yu Suponitsky 2
Kirill Yu Suponitsky
, 
10.1016/j.mencom.2014.11.011
Published 2014-10-30
Communication , Volume 24, Issue 6, 346-348
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Novikov R. A. et al. Unexpected formation of substituted naphthalenes and phenanthrenes in a GaCl3 mediated dimerization–fragmentation reaction of 2-arylcyclopropane-1,1-dicarboxylates // Mendeleev Communications. 2014. Vol. 24. No. 6. pp. 346-348.
GOST all authors (up to 50) Copy
Novikov R. A., Tarasova A. V., Suponitsky K. Yu., Tomilov Y. V. Unexpected formation of substituted naphthalenes and phenanthrenes in a GaCl3 mediated dimerization–fragmentation reaction of 2-arylcyclopropane-1,1-dicarboxylates // Mendeleev Communications. 2014. Vol. 24. No. 6. pp. 346-348.
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TY - JOUR
DO - 10.1016/j.mencom.2014.11.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.11.011
TI - Unexpected formation of substituted naphthalenes and phenanthrenes in a GaCl3 mediated dimerization–fragmentation reaction of 2-arylcyclopropane-1,1-dicarboxylates
T2 - Mendeleev Communications
AU - Novikov, Roman Aleksandrovich
AU - Tarasova, Anna Vadimovna
AU - Suponitsky, Kirill Yu
AU - Tomilov, Yury Vasil'evich
PY - 2014
DA - 2014/10/30
PB - Mendeleev Communications
SP - 346-348
IS - 6
VL - 24
ER -
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@article{2014_Novikov,
author = {Roman Aleksandrovich Novikov and Anna Vadimovna Tarasova and Kirill Yu Suponitsky and Yury Vasil'evich Tomilov},
title = {Unexpected formation of substituted naphthalenes and phenanthrenes in a GaCl3 mediated dimerization–fragmentation reaction of 2-arylcyclopropane-1,1-dicarboxylates},
journal = {Mendeleev Communications},
year = {2014},
volume = {24},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.11.011},
number = {6},
pages = {346--348},
doi = {10.1016/j.mencom.2014.11.011}
}
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Novikov, Roman Aleksandrovich, et al. “Unexpected formation of substituted naphthalenes and phenanthrenes in a GaCl3 mediated dimerization–fragmentation reaction of 2-arylcyclopropane-1,1-dicarboxylates.” Mendeleev Communications, vol. 24, no. 6, Oct. 2014, pp. 346-348. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.11.011.

Abstract

Dimethyl 2-arylcyclopropane-1,1-dicarboxylates on heating with GaCl3 undergo dimerization to afford arylnaphthalenes or phenanthrenes. A possible reaction mechanism including elimination of two dimethyl malonate molecules was proposed, dimethyl malonate gallium complex Ga3+[H2C(CO2Me)2]3(GaCl–) was isolated and characterized by X-ray diffraction analysis.

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