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Chlorovinylidenecarbene: Generation from 3,3-Dichloropropyne by Base Solvolysis (under Phase-transfer Catalysis Conditions) and Reaction with Alkenes

Konstantin Nikolaevich Shavrin 1
Konstantin Nikolaevich Shavrin
, 
Inna Borisovna Shvedova 1
Inna Borisovna Shvedova
, 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
10.1070/MC1993v003n02ABEH000217
Published 1993-04-30
Communication , Volume 3, Issue 2, 50-51
6
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Shavrin K. N., Shvedova I. B., Nefedov O. M. Chlorovinylidenecarbene: Generation from 3,3-Dichloropropyne by Base Solvolysis (under Phase-transfer Catalysis Conditions) and Reaction with Alkenes // Mendeleev Communications. 1993. Vol. 3. No. 2. pp. 50-51.
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Shavrin K. N., Shvedova I. B., Nefedov O. M. Chlorovinylidenecarbene: Generation from 3,3-Dichloropropyne by Base Solvolysis (under Phase-transfer Catalysis Conditions) and Reaction with Alkenes // Mendeleev Communications. 1993. Vol. 3. No. 2. pp. 50-51.
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TY - JOUR
DO - 10.1070/MC1993v003n02ABEH000217
UR - https://mendcomm.colab.ws/publications/10.1070/MC1993v003n02ABEH000217
TI - Chlorovinylidenecarbene: Generation from 3,3-Dichloropropyne by Base Solvolysis (under Phase-transfer Catalysis Conditions) and Reaction with Alkenes
T2 - Mendeleev Communications
AU - Shavrin, Konstantin Nikolaevich
AU - Shvedova, Inna Borisovna
AU - Nefedov, Oleg Matveevich
PY - 1993
DA - 1993/04/30
PB - Mendeleev Communications
SP - 50-51
IS - 2
VL - 3
ER -
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@article{1993_Shavrin,
author = {Konstantin Nikolaevich Shavrin and Inna Borisovna Shvedova and Oleg Matveevich Nefedov},
title = {Chlorovinylidenecarbene: Generation from 3,3-Dichloropropyne by Base Solvolysis (under Phase-transfer Catalysis Conditions) and Reaction with Alkenes},
journal = {Mendeleev Communications},
year = {1993},
volume = {3},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1993v003n02ABEH000217},
number = {2},
pages = {50--51},
doi = {10.1070/MC1993v003n02ABEH000217}
}
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Shavrin, Konstantin Nikolaevich, et al. “Chlorovinylidenecarbene: Generation from 3,3-Dichloropropyne by Base Solvolysis (under Phase-transfer Catalysis Conditions) and Reaction with Alkenes.” Mendeleev Communications, vol. 3, no. 2, Apr. 1993, pp. 50-51. https://mendcomm.colab.ws/publications/10.1070/MC1993v003n02ABEH000217.

Abstract

The chlorovinylidenecarbene 6 has been generated from 3,3-dichloropropyne 1a via γ-elimination of hydrogen chloride on treatment with powdered KOH under phase-transfer catalysis conditions and has been trapped by alkenes, to form chlorovinylidenecyclopropanes 7 in 20–45% yields.

References

1.
Alkynylhalocarbenes: generation from 1,1-dihaloalk-2-ynes by base solvolysis and reaction with alkenes
Shavrin K.N., Krylova I.V., Shvedova I.B., Okonnishnikova G.P., Dolgy I.E., Nefedov O.M.
Journal of the Chemical Society Perkin Transactions 2, 1991
2.
10.1070/MC1993v003n02ABEH000217_bib2
Kirmse
Carbene Chemistry, 1971
3.
Unsaturated carbenes
Stang P.J.
Chemical Reviews, 1978