Home / Publications / Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions

Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions

Olesya Igorevna Militsina 1
Olesya Igorevna Militsina
, 
Galina Ivanovna Kovyljaeva 1
Galina Ivanovna Kovyljaeva
, 
Galina Azikovna Bakaleynik 1
Galina Azikovna Bakaleynik
, 
Irina Yuryevna Strobykina 1
Irina Yuryevna Strobykina
, 
Vladimir Evgenievich Kataev 1
Vladimir Evgenievich Kataev
, 
Vladimir Alekseevich Alfonsov 1
Vladimir Alekseevich Alfonsov
, 
Rashid Zagitovich Musin 1
Rashid Zagitovich Musin
, 
Dmitry Valer'evich Beskrovny 1
Dmitry Valer'evich Beskrovny
, 
Igor Anatol'evich Litvinov 1
Igor Anatol'evich Litvinov
10.1070/MC2005v015n01ABEH001946
Published 2005-02-09
Communication , Volume 15, Issue 1, 27-29
9
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Militsina O. I. et al. Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions // Mendeleev Communications. 2005. Vol. 15. No. 1. pp. 27-29.
GOST all authors (up to 50) Copy
Militsina O. I., Kovyljaeva G. I., Bakaleynik G. A., Strobykina I. Y., Kataev V. E., Alfonsov V. A., Musin R. Z., Beskrovny D. V., Litvinov I. A. Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions // Mendeleev Communications. 2005. Vol. 15. No. 1. pp. 27-29.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC2005v015n01ABEH001946
UR - https://mendcomm.colab.ws/publications/10.1070/MC2005v015n01ABEH001946
TI - Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions
T2 - Mendeleev Communications
AU - Militsina, Olesya Igorevna
AU - Kovyljaeva, Galina Ivanovna
AU - Bakaleynik, Galina Azikovna
AU - Strobykina, Irina Yuryevna
AU - Kataev, Vladimir Evgenievich
AU - Alfonsov, Vladimir Alekseevich
AU - Musin, Rashid Zagitovich
AU - Beskrovny, Dmitry Valer'evich
AU - Litvinov, Igor Anatol'evich
PY - 2005
DA - 2005/02/09
PB - Mendeleev Communications
SP - 27-29
IS - 1
VL - 15
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2005_Militsina,
author = {Olesya Igorevna Militsina and Galina Ivanovna Kovyljaeva and Galina Azikovna Bakaleynik and Irina Yuryevna Strobykina and Vladimir Evgenievich Kataev and Vladimir Alekseevich Alfonsov and Rashid Zagitovich Musin and Dmitry Valer'evich Beskrovny and Igor Anatol'evich Litvinov},
title = {Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions},
journal = {Mendeleev Communications},
year = {2005},
volume = {15},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2005v015n01ABEH001946},
number = {1},
pages = {27--29},
doi = {10.1070/MC2005v015n01ABEH001946}
}
MLA
Cite this
MLA Copy
Militsina, Olesya Igorevna, et al. “Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions.” Mendeleev Communications, vol. 15, no. 1, Feb. 2005, pp. 27-29. https://mendcomm.colab.ws/publications/10.1070/MC2005v015n01ABEH001946.

Abstract

Heating the 16-E-oxime of isosteviol (ent-16-E-hydroxyiminobeyeran-19-oic acid) with concentrated hydrochloric acid (or 25% H2SO4) at 110 °C leads to the formation of lactone of 4α-carboxy-13α-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid as the main product, whereas approximately equal quantities of this lactone and lactam of 4α-carboxy-13α-amino-13,16-seco-ent-19-norbeyeran-16-oic acid are formed by heating the 16-E-oxime of isosteviol with concentrated hydrochloric acid in an ampoule at 180 °C.

References

1.
10.1070/MC2005v015n01ABEH001946_bib1
Donoruma
1960
2.
10.1070/MC2005v015n01ABEH001946_bib2
Smith
Molecular Rearrangements, 1962
3.
10.1070/MC2005v015n01ABEH001946_bib3
McCarty
The Chemistry of the Carbon–Nitrogen Double Bond, 1970
6.
10.1070/MC2005v015n01ABEH001946_bib6
Soloducho
Pol. J. Chem., 1979
7.
10.1070/MC2005v015n01ABEH001946_bib7
Kozlov
Zh. Org. Khim., 1982
8.
10.1070/MC2005v015n01ABEH001946_bib8
Hanson
The Tetracyclic Diterpenes, 1968
9.
10.1070/MC2005v015n01ABEH001946_bib9
MacMillan
1999
11.
10.1070/MC2005v015n01ABEH001946_bib11
Alfonsov
Zh. Obshch. Khim., 1998
13.
10.1070/MC2005v015n01ABEH001946_bib13
Alfonsov
Zh. Obshch. Khim., 2003