Solvent-induced allylic rearrangements in poly(trichlorobutadiene) chains

Lebedeva, T. L.; Vointseva, I.I.; Gil'man, L. M.; Petrovskii, P. V.; Larina, T.A.

doi:10.1007/bf02495203

Cited by 3 publications

(1 citation statement)

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“…The literature reports occurrence of olefinic and allylic hydrogen rearrangements in the presence of CDCl 3 , but those reactions were purposely carried out under acidic conditions to study the behavior of compounds [ 14 , 15 , 16 ]. In the case at hand the transformation of compound 4 into 7 is undoubtedly due to traces of DCl, which is always present in commercial CDCl 3 , unless the solvent is passed through basic alumina (acidity I) immediately before use.…”

Section: Introductionmentioning

confidence: 99%

Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy

et al. 2009

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Friedelin (1), 3β-friedelinol (2), 28-hydroxyfriedelin (3), 16α-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16α,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl3 solution, 16α-hydroxyfriedelin (4) reacted turning into 3-oxo-16-methylfriedel-16-ene (7). This is the first report of a dehydration followed by a Nametkin rearrangement of a pentacyclic triterpene in CDCl3 solution occurring in the NMR tube. These seven pentacyclic triterpenes was identified through NMR spectroscopy and the stereochemistry of compound 4 and 7 was established by 2D NMR (NOESY) spectroscopy and mass spectrometry (GC-MS). It is also the first time that all the 13C-NMR and 2D NMR spectral data are reported for compounds 4 and 7.

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Section: Introductionmentioning

confidence: 99%

Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy

et al. 2009

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Allylic Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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In allylic rearrangement, and occasionally referred to as the allylic isomerization, allylic transposition, and allylic 1,3‐rearrangement, migration of a carboncarbon double bond within a three‐carbon system (i.e., allylic), often occurring on the nucelophilic substitution of allylic systems in which the nucleophile adds to the carbon‐carbon double bond along with the cleavage of the allylic leaving group. The allylic rearrangement is also known as the S N 1′ or S N 2′ reaction. This reaction has been found to be promoted by light, enzymes, solvents, acid, (especially the Lewis acids such as Eu(fod) PBr and NiCl 2 ) and transition metal catalysts (including tungsten, rhodium, cobalt and palladium). The allylic rearrangement has been extensively used to synthesize a variety of organic molecules.

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The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems

2016

Spectroscopy

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Friedelin (1), 3β-friedelinol (2), 28-hydroxyfriedelin (3), 16α-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16α,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl 3 solution, 16α-hydroxyfriedelin (4) reacted turning into 3-oxo-16-methylfriedel-16-ene (7). This is the first report of a dehydration followed by a Nametkin rearrangement of a pentacyclic triterpene in CDCl 3 solution occurring in the NMR tube. These seven pentacyclic triterpenes was identified through NMR spectroscopy and the stereochemistry of compound 4 and 7 was established by 2D NMR (NOESY) spectroscopy and mass spectrometry (GC-MS). It is also the first time that all the 13 C-NMR and 2DNMR spectral data are reported for compounds 4 and 7.

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Solvent-induced allylic rearrangements in poly(trichlorobutadiene) chains

Cited by 3 publications

References 1 publication

Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy

Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy

Allylic Rearrangement

The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems

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