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Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones

Vladimir Anatol'evich Ogurtsov 1
Vladimir Anatol'evich Ogurtsov
, 
Oleg Alexeevich Rakitin 1
Oleg Alexeevich Rakitin
, 
Charles W Rees 2
Charles W Rees
, 
Alexey Aleksandrovich Smolentsev 1
Alexey Aleksandrovich Smolentsev
10.1070/MC2005v015n02ABEH002086
Published 2005-03-23
Communication , Volume 15, Issue 2, 55-56
11
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Ogurtsov V. A. et al. Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones // Mendeleev Communications. 2005. Vol. 15. No. 2. pp. 55-56.
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Ogurtsov V. A., Rakitin O. A., Rees C. W., Smolentsev A. A. Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones // Mendeleev Communications. 2005. Vol. 15. No. 2. pp. 55-56.
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TY - JOUR
DO - 10.1070/MC2005v015n02ABEH002086
UR - https://mendcomm.colab.ws/publications/10.1070/MC2005v015n02ABEH002086
TI - Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones
T2 - Mendeleev Communications
AU - Ogurtsov, Vladimir Anatol'evich
AU - Rakitin, Oleg Alexeevich
AU - Rees, Charles W
AU - Smolentsev, Alexey Aleksandrovich
PY - 2005
DA - 2005/03/23
PB - Mendeleev Communications
SP - 55-56
IS - 2
VL - 15
ER -
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@article{2005_Ogurtsov,
author = {Vladimir Anatol'evich Ogurtsov and Oleg Alexeevich Rakitin and Charles W Rees and Alexey Aleksandrovich Smolentsev},
title = {Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones},
journal = {Mendeleev Communications},
year = {2005},
volume = {15},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2005v015n02ABEH002086},
number = {2},
pages = {55--56},
doi = {10.1070/MC2005v015n02ABEH002086}
}
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Ogurtsov, Vladimir Anatol'evich, et al. “Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones.” Mendeleev Communications, vol. 15, no. 2, Mar. 2005, pp. 55-56. https://mendcomm.colab.ws/publications/10.1070/MC2005v015n02ABEH002086.

Abstract

The thiocarbonyl group of 4,5-dichloro-1,2-dithiole-3-thione reacts as a 1,3-dipolarophile towards diaryl nitrile imines by 1,3-dipolar cycloaddition followed by opening of the dithiole ring with loss of sulfur to give 5-methylene-1,3,4-thiadiazolines; this reaction together with nucleophilic displacement (before or after cycloaddition) of the selectively reactive 5-chlorine atom provides a rapid access to stable 5-methylene-1,3,4-thiadiazolines.

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