Home / Publications / An unusual Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene

An unusual Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene

Vladimir V Khripach 1
Vladimir V Khripach
, 
Vladimir Nikolaevich Zhabinskii 1
Vladimir Nikolaevich Zhabinskii
, 
Anna Ivanovna Kotyatkina 1
Anna Ivanovna Kotyatkina
, 
Galina Pavlovna Fando 1
Galina Pavlovna Fando
, 
Alexander S Lyakhov 1
Alexander S Lyakhov
, 
Alla A Govorova 1
Alla A Govorova
, 
Jaap van der Louw 2
Jaap van der Louw
, 
Marinus B Groen 2
Marinus B Groen
, 
Aede de Groot 3
Aede de Groot
10.1070/MC2001v011n04ABEH001448
Published 2001-08-01
Communication , Volume 11, Issue 4, 144-145
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Khripach V. V. et al. An unusual Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene // Mendeleev Communications. 2001. Vol. 11. No. 4. pp. 144-145.
GOST all authors (up to 50) Copy
Khripach V. V., Zhabinskii V. N., Kotyatkina A. I., Fando G. P., Lyakhov A. S., Govorova A. A., van der Louw J., Groen M. B., de Groot A. An unusual Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene // Mendeleev Communications. 2001. Vol. 11. No. 4. pp. 144-145.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC2001v011n04ABEH001448
UR - https://mendcomm.colab.ws/publications/10.1070/MC2001v011n04ABEH001448
TI - An unusual Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene
T2 - Mendeleev Communications
AU - Khripach, Vladimir V
AU - Zhabinskii, Vladimir Nikolaevich
AU - Kotyatkina, Anna Ivanovna
AU - Fando, Galina Pavlovna
AU - Lyakhov, Alexander S
AU - Govorova, Alla A
AU - van der Louw, Jaap
AU - Groen, Marinus B
AU - de Groot, Aede
PY - 2001
DA - 2001/08/01
PB - Mendeleev Communications
SP - 144-145
IS - 4
VL - 11
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2001_Khripach,
author = {Vladimir V Khripach and Vladimir Nikolaevich Zhabinskii and Anna Ivanovna Kotyatkina and Galina Pavlovna Fando and Alexander S Lyakhov and Alla A Govorova and Jaap van der Louw and Marinus B Groen and Aede de Groot},
title = {An unusual Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene},
journal = {Mendeleev Communications},
year = {2001},
volume = {11},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2001v011n04ABEH001448},
number = {4},
pages = {144--145},
doi = {10.1070/MC2001v011n04ABEH001448}
}
MLA
Cite this
MLA Copy
Khripach, Vladimir V., et al. “An unusual Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene.” Mendeleev Communications, vol. 11, no. 4, Aug. 2001, pp. 144-145. https://mendcomm.colab.ws/publications/10.1070/MC2001v011n04ABEH001448.

Abstract

The Bamford–Stevens reaction of 17-toluenesulfonylhydrazono-3β-acetoxy-14α-hydroxyandrost-5-ene was found to proceed with migration of the 18-methyl group and formation of a 13,14-epoxide.

References

1.
10.1070/MC2001v011n04ABEH001448_bib1
Bamford
J. Org. Chem., 1952
2.
The Rearrangement of the Steroid C/D Rings1
Hirschmann R., Snoddy C.S., Hiskey C.F., Wendler N.L.
Journal of the American Chemical Society, 1954
3.
Studies on C-nor-D-homosteroids—VIII
Mitsuhashi H., Shimizu Y., Kawahara N.
Tetrahedron, 1968
4.
10.1070/MC2001v011n04ABEH001448_bib4
Cagliotti
Gazz. Chim. Ital., 1964
5.
A Steroidal Internal Displacement Reaction1
Tanabe M., Crowe D.F.
Journal of Organic Chemistry, 1963
7.
10.1070/MC2001v011n04ABEH001448_bib7
Allen
Chemical Design Automation News, 1993
8.
Retropinacol Rearrangement of Estradiol 3-Methyl Ether
JOHNS W.F.
Journal of Organic Chemistry, 1961
9.
SIR97: a new tool for crystal structure determination and refinement
Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G., Polidori G., Spagna R.
Journal of Applied Crystallography, 1999
10.
G. M. Sheldrick. Program for Crystal Structure Refinement, University of Göttingen, 1997.