Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton

Tanase, Constantin I.; Hanganu, Anamaria; Draghici, Constantin

Constantin I. Tanase, Anamaria Hanganu, Constantin Draghici

Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton

Abstract:

TFA was added to a solution of a bicyclo[2.2.1]heptane azide-alcohol in CDCl3 to correctly characterize the compound, but during 24 h gave the trifluoro acetylated compound in quantitative yield. NMR spectra of the esterified compound helped us also to correctly attribute the NMR signals to the protons, and also confirmed the identification of the carbon atoms. The study was extended to other 14 compounds containing a primary alcohol group alone or with an ethylene ketal, a δ- or -lactone group, a primary and a secondary group, two primary and an alkene group and two primary and a secondary alcohol groups on scaffolds containing bicyclo[2.2.1]heptane, oxabicyclo[3.3.0]octane, bicyclo [2.2.1]heptane constrained with a cyclopropane ring and bicyclo[3.3.0]octane fragments. The esterification of all compounds was also quantitative in 24 to 72 h; this helped us to correct attribute the NMR signals to the protons and carbon atoms of the un-esterified compounds by comparison with those of the trifluoro acetylated compounds. A graphical presentation of 1H- and 13C-NMR spectra of a few un-esterified and esterified compounds are presented in the paper.

Keywords:
CF3COOH; alcohols esterification; NMR tube trifluoroacetylation; bicyclo<2.2.1>heptane alcohols; oxabicyclo<3.3.0>octane; Corey lactol; bicyclo<3.3.0>octane; prostaglandin enone; prostaglandin diols

Issue: 2021, Volume 72, Issue 2

Pages: 156-177

Publication date: 2021/5/7

https://doi.org/10.37358/RC.21.2.8428

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
TANASE, C.I., HANGANU, A., DRAGHICI, C., Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton, Rev. Chim., 72(2), 2021, 156-177.

Vancouver
Tanase CI, Hanganu A, Draghici C. Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton. Rev. Chim.[internet]. 2021 Feb;72(2):156-177. Available from: https://doi.org/10.37358/RC.21.2.8428

APA 6th edition
Tanase, C.I., Hanganu, A. & Draghici, C. (2021). Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton. Revista de Chimie, 72(2), 156-177. https://doi.org/10.37358/RC.21.2.8428

Harvard
Tanase, C.I., Hanganu, A., Draghici, C. (2021). 'Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton', Revista de Chimie, 72(2), pp. 156-177. https://doi.org/10.37358/RC.21.2.8428

IEEE
C.I. Tanase, A. Hanganu, C. Draghici, "Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton". Revista de Chimie, vol. 72, no. 2, pp. 156-177, 2021. [online]. https://doi.org/10.37358/RC.21.2.8428

Text
Constantin I. Tanase, Anamaria Hanganu, Constantin Draghici,
Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton,
Revista de Chimie,
Volume 72, Issue 2,
2021,
Pages 156-177,
ISSN 2668-8212,
https://doi.org/10.37358/RC.21.2.8428.
(https://revistadechimie.ro/Articles.asp?ID=8428)
Keywords: CF3COOH; alcohols esterification; NMR tube trifluoroacetylation; bicyclo<2.2.1>heptane alcohols; oxabicyclo<3.3.0>octane; Corey lactol; bicyclo<3.3.0>octane; prostaglandin enone; prostaglandin diols

RIS
TY - JOUR
T1 - Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton
A1 - Tanase, Constantin I.
A2 - Hanganu, Anamaria
A3 - Draghici, Constantin
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2021
VL - 72
IS - 2
SP - 156
EP - 177
UR - https://doi.org/10.37358/RC.21.2.8428
KW - CF3COOH
KW - alcohols esterification
KW - NMR tube trifluoroacetylation
KW - bicyclo<2.2.1>heptane alcohols
KW - oxabicyclo<3.3.0>octane
KW - Corey lactol
KW - bicyclo<3.3.0>octane
KW - prostaglandin enone
KW - prostaglandin diols
ER -

BibTex
@article{RevCh2021P156,
author = {Tanase Constantin I. and Hanganu Anamaria and Draghici Constantin},
title = {Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo<2.2.1>heptane, Oxabicyclo<3.3.0>octane and Bicyclo<3.3.0>octane Skeleton},
journal = {Revista de Chimie},
volume = {72},
number = {2},
pages = {156-177},
year = {2021},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.21.2.8428},
url = {https://revistadechimie.ro/Articles.asp?ID=8428}
}

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