Home / Publications / Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane

Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane

Alexey V Kalinin 1
Alexey V Kalinin
, 
Evgenii Abramovich Shapiro 1
Evgenii Abramovich Shapiro
,  , 
Bogdan Ivanovich Ugrak 1
Bogdan Ivanovich Ugrak
, 
Aristidis M Tsatsakis 2
Aristidis M Tsatsakis
, 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
2 The School of Health Sciences, University of Crete, Iraklion, Crete, Greece
10.1070/MC1993v003n05ABEH000281
Published 1993-10-30
Communication , Volume 3, Issue 5, 190-191
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kalinin A. V. et al. Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane // Mendeleev Communications. 1993. Vol. 3. No. 5. pp. 190-191.
GOST all authors (up to 50) Copy
Kalinin A. V., Shapiro E. A., Tomilov Y. V., Ugrak B. I., Tsatsakis A. M., Nefedov O. M. Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane // Mendeleev Communications. 1993. Vol. 3. No. 5. pp. 190-191.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC1993v003n05ABEH000281
UR - https://mendcomm.colab.ws/publications/10.1070/MC1993v003n05ABEH000281
TI - Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane
T2 - Mendeleev Communications
AU - Kalinin, Alexey V
AU - Shapiro, Evgenii Abramovich
AU - Tomilov, Yury Vasil'evich
AU - Ugrak, Bogdan Ivanovich
AU - Tsatsakis, Aristidis M
AU - Nefedov, Oleg Matveevich
PY - 1993
DA - 1993/10/30
PB - Mendeleev Communications
SP - 190-191
IS - 5
VL - 3
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{1993_Kalinin,
author = {Alexey V Kalinin and Evgenii Abramovich Shapiro and Yury Vasil'evich Tomilov and Bogdan Ivanovich Ugrak and Aristidis M Tsatsakis and Oleg Matveevich Nefedov},
title = {Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane},
journal = {Mendeleev Communications},
year = {1993},
volume = {3},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1993v003n05ABEH000281},
number = {5},
pages = {190--191},
doi = {10.1070/MC1993v003n05ABEH000281}
}
MLA
Cite this
MLA Copy
Kalinin, Alexey V., et al. “Selective Non-catalytic Cyclopropanation of Methyl (E)-Pent-3-en-1-yn-3-ylcarboxylates with Diazomethane.” Mendeleev Communications, vol. 3, no. 5, Oct. 1993, pp. 190-191. https://mendcomm.colab.ws/publications/10.1070/MC1993v003n05ABEH000281.

Abstract

1,3-Dipolar cycloaddition of diazomethane to methyl (E)-pent-3-en-1-yn-3-ylcarboxylates proceeds selectively with participation of only the double bond, resulting in unstable methyl 3-alkynylpyrazolinylcarboxylates, thermolysis of which leads to methyl 1-alkynylcyclopropanecarboxylates and 4-methylpent-3-en-1-yn-3-ylcarboxylates.

References

1.
10.1070/MC1993v003n05ABEH000281_bib1
Regitz
1984
3.
Enantioselective synthesis of the epoxy diyne core of neocarzinostatin chromophore
Myers A.G., Harrington P.M., Kuo E.Y.
Journal of the American Chemical Society, 1991