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An unusually easy [1,3]-migration of the PhS group in 3-methyl-4-phenylthiohept-2-en-1-ols

Natalia Yakovlevna Grigorieva 1
Natalia Yakovlevna Grigorieva
, 
Paata Grigor'evich Tsiklauri 1
Paata Grigor'evich Tsiklauri
, 
Alexei Viktorovich Buevich 1
Alexei Viktorovich Buevich
10.1070/MC1998v008n02ABEH000924
Published 1998-04-28
Communication , Volume 8, Issue 2, 76-77
2
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Grigorieva N. Y., Tsiklauri P. G., Buevich A. V. An unusually easy [1,3]-migration of the PhS group in 3-methyl-4-phenylthiohept-2-en-1-ols // Mendeleev Communications. 1998. Vol. 8. No. 2. pp. 76-77.
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Grigorieva N. Y., Tsiklauri P. G., Buevich A. V. An unusually easy [1,3]-migration of the PhS group in 3-methyl-4-phenylthiohept-2-en-1-ols // Mendeleev Communications. 1998. Vol. 8. No. 2. pp. 76-77.
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TY - JOUR
DO - 10.1070/MC1998v008n02ABEH000924
UR - https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000924
TI - An unusually easy [1,3]-migration of the PhS group in 3-methyl-4-phenylthiohept-2-en-1-ols
T2 - Mendeleev Communications
AU - Grigorieva, Natalia Yakovlevna
AU - Tsiklauri, Paata Grigor'evich
AU - Buevich, Alexei Viktorovich
PY - 1998
DA - 1998/04/28
PB - Mendeleev Communications
SP - 76-77
IS - 2
VL - 8
ER -
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@article{1998_Grigorieva,
author = {Natalia Yakovlevna Grigorieva and Paata Grigor'evich Tsiklauri and Alexei Viktorovich Buevich},
title = {An unusually easy [1,3]-migration of the PhS group in 3-methyl-4-phenylthiohept-2-en-1-ols},
journal = {Mendeleev Communications},
year = {1998},
volume = {8},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000924},
number = {2},
pages = {76--77},
doi = {10.1070/MC1998v008n02ABEH000924}
}
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Grigorieva, Natalia Yakovlevna, et al. “An unusually easy [1,3]-migration of the PhS group in 3-methyl-4-phenylthiohept-2-en-1-ols.” Mendeleev Communications, vol. 8, no. 2, Apr. 1998, pp. 76-77. https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000924.

Abstract

Hydride reduction of the 2(Z)- and 2(E)-isomers of methyl and tert-butyl 3-methyl-4-phenylthioheptenoates under standard conditions is accompanied by [1,3]-migration of the PhS group and in both cases (E)-3-methyl-2-phenylthiohept-3-en-1-ol 5 is produced, whose structure is confirmed by spectroscopic methods, instead of the expected (Z)-3-methyl-4-phenylthiohept-2- 3a and (E)-2-enol 3b; compounds 3a,b obtained under specially developed conditions undergo isomerisation to compound 5 during chromatography on SiO2 or on storage in the light of their solutions in CDCl3 or in C6D6.

References

1.
Mechanism of the [1,3] phenylthio shift in the rearrangement of allyl sulphides
Brownbridge P., Warren S.
Journal of the Chemical Society Perkin Transactions 1, 1976
2.
N.Ya. Grigor’eva, P. G. Tsiklauri, O. A. Pinsker and A. V. Buevich, Izv. Akad. Nauk, Ser. Khim., 1998 (in press).
3.
Grigorieva N.Y., Pinsker O.A., Moiseenkov A.M.
Mendeleev Communications, 1994