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Selective Catalytic Methoxycarbonylmethylenation of the Triple Bond of Vinylacetylene with Methyl Diazoacetate

Evgenii Abramovich Shapiro 1
Evgenii Abramovich Shapiro
, 
Alexey V Kalinin 1
Alexey V Kalinin
, 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
10.1070/MC1992v002n03ABEH000163
Published 1992-09-30
Communication , Volume 2, Issue 3, 116-117
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Shapiro E. A., Kalinin A. V., Nefedov O. M. Selective Catalytic Methoxycarbonylmethylenation of the Triple Bond of Vinylacetylene with Methyl Diazoacetate // Mendeleev Communications. 1992. Vol. 2. No. 3. pp. 116-117.
GOST all authors (up to 50) Copy
Shapiro E. A., Kalinin A. V., Nefedov O. M. Selective Catalytic Methoxycarbonylmethylenation of the Triple Bond of Vinylacetylene with Methyl Diazoacetate // Mendeleev Communications. 1992. Vol. 2. No. 3. pp. 116-117.
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TY - JOUR
DO - 10.1070/MC1992v002n03ABEH000163
UR - https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000163
TI - Selective Catalytic Methoxycarbonylmethylenation of the Triple Bond of Vinylacetylene with Methyl Diazoacetate
T2 - Mendeleev Communications
AU - Shapiro, Evgenii Abramovich
AU - Kalinin, Alexey V
AU - Nefedov, Oleg Matveevich
PY - 1992
DA - 1992/09/30
PB - Mendeleev Communications
SP - 116-117
IS - 3
VL - 2
ER -
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@article{1992_Shapiro,
author = {Evgenii Abramovich Shapiro and Alexey V Kalinin and Oleg Matveevich Nefedov},
title = {Selective Catalytic Methoxycarbonylmethylenation of the Triple Bond of Vinylacetylene with Methyl Diazoacetate},
journal = {Mendeleev Communications},
year = {1992},
volume = {2},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000163},
number = {3},
pages = {116--117},
doi = {10.1070/MC1992v002n03ABEH000163}
}
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Shapiro, Evgenii Abramovich, et al. “Selective Catalytic Methoxycarbonylmethylenation of the Triple Bond of Vinylacetylene with Methyl Diazoacetate.” Mendeleev Communications, vol. 2, no. 3, Sep. 1992, pp. 116-117. https://mendcomm.colab.ws/publications/10.1070/MC1992v002n03ABEH000163.

Abstract

Selective RH2(OAc)4-promoted methoxycarbonylmethylenation of the triple bond of vinylacetylene with methyl diazoacetate results in methyl 1-vinylcyclopropene-3-carboxylate 1, which [2 + 2]cyclodimerizes in situ to give dimethyl trans-1, 2-divinyltricyclo[3.1.0.02,4]hexane-3,6-dicarboxylate 2.

References

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E. A. Shapiro, A. V. Kalinin and O. M. Nefedov, Org. Proc. Prep. Int., 1992, in the press.
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M. P. Doyle (Trinity University, San Antonio, Texas), personal communication.
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Photodimerization of some cyclopropenes
DeBoer C.D., Wadsworth D.H., Perkins W.C.
Journal of the American Chemical Society, 1973