Home / Publications / Nucleophilic Substitution in the Allyl System of Codeine and Pseudocodeine in their Reactions with Lithium Methyl- and Aryl-cyanocuprates. Crystal and Molecular Structure of 8α-Phenyl-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-Phenyl-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan

Nucleophilic Substitution in the Allyl System of Codeine and Pseudocodeine in their Reactions with Lithium Methyl- and Aryl-cyanocuprates. Crystal and Molecular Structure of 8α-Phenyl-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-Phenyl-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan

Valery Nikolaevich Kalinin 1
Valery Nikolaevich Kalinin
, 
Irina Leonidovna Belyakova 1
Irina Leonidovna Belyakova
, 
Vladimir Vasil'evich Kobak 1
Vladimir Vasil'evich Kobak
, 
Pavel Vasil'evich Petrovskii 1
Pavel Vasil'evich Petrovskii
, 
Aleksandr Il'ich Yanovsky 1
Aleksandr Il'ich Yanovsky
, 
Yuri Timofeevich Struchkov 1
Yuri Timofeevich Struchkov
10.1070/MC1993v003n01ABEH000197
Published 1993-02-28
Communication , Volume 3, Issue 1, 12-13
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Kalinin V. N. et al. Nucleophilic Substitution in the Allyl System of Codeine and Pseudocodeine in their Reactions with Lithium Methyl- and Aryl-cyanocuprates. Crystal and Molecular Structure of 8α-Phenyl-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-Phenyl-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan // Mendeleev Communications. 1993. Vol. 3. No. 1. pp. 12-13.
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Kalinin V. N., Belyakova I. L., Kobak V. V., Petrovskii P. V., Yanovsky A. I., Struchkov Y. T. Nucleophilic Substitution in the Allyl System of Codeine and Pseudocodeine in their Reactions with Lithium Methyl- and Aryl-cyanocuprates. Crystal and Molecular Structure of 8α-Phenyl-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-Phenyl-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan // Mendeleev Communications. 1993. Vol. 3. No. 1. pp. 12-13.
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TY - JOUR
DO - 10.1070/MC1993v003n01ABEH000197
UR - https://mendcomm.colab.ws/publications/10.1070/MC1993v003n01ABEH000197
TI - Nucleophilic Substitution in the Allyl System of Codeine and Pseudocodeine in their Reactions with Lithium Methyl- and Aryl-cyanocuprates. Crystal and Molecular Structure of 8α-Phenyl-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-Phenyl-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan
T2 - Mendeleev Communications
AU - Kalinin, Valery Nikolaevich
AU - Belyakova, Irina Leonidovna
AU - Kobak, Vladimir Vasil'evich
AU - Petrovskii, Pavel Vasil'evich
AU - Yanovsky, Aleksandr Il'ich
AU - Struchkov, Yuri Timofeevich
PY - 1993
DA - 1993/02/28
PB - Mendeleev Communications
SP - 12-13
IS - 1
VL - 3
ER -
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@article{1993_Kalinin,
author = {Valery Nikolaevich Kalinin and Irina Leonidovna Belyakova and Vladimir Vasil'evich Kobak and Pavel Vasil'evich Petrovskii and Aleksandr Il'ich Yanovsky and Yuri Timofeevich Struchkov},
title = {Nucleophilic Substitution in the Allyl System of Codeine and Pseudocodeine in their Reactions with Lithium Methyl- and Aryl-cyanocuprates. Crystal and Molecular Structure of 8α-Phenyl-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-Phenyl-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan},
journal = {Mendeleev Communications},
year = {1993},
volume = {3},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1993v003n01ABEH000197},
number = {1},
pages = {12--13},
doi = {10.1070/MC1993v003n01ABEH000197}
}
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Kalinin, Valery Nikolaevich, et al. “Nucleophilic Substitution in the Allyl System of Codeine and Pseudocodeine in their Reactions with Lithium Methyl- and Aryl-cyanocuprates. Crystal and Molecular Structure of 8α-Phenyl-6,7-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-Phenyl-7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan.” Mendeleev Communications, vol. 3, no. 1, Feb. 1993, pp. 12-13. https://mendcomm.colab.ws/publications/10.1070/MC1993v003n01ABEH000197.

Abstract

It has been shown that nucleophilic substitution in 6β-chloro-7,8-didehydro-4,5α-epoxy-3-rnethoxy-17-methylmorphinan and 8β-bromo-6,7-didehydro-4,5α-epoxy-3-rnethoxy-17-methylmorphinan is accompanied by allylic rearrangement with both a change in and retention of the orientation of the substituting group. X-Ray diffraction studies of 8α-phenyl-6,7-didehydro- 4,5α-epoxy-3-methoxy-17-methylmorphinan and 6β-phenyl-7,8-didehydro-4,5α-epoxy-3-rnethoxy-17-methylmorphinan have been carried out.1Fax: +7 095 135 5085.

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