Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis

Antonioletti, Roberto; Bonadies, F.; Ciammaichella, A; Viglianti, Angela

doi:10.1016/j.tet.2008.02.091

Cited by 31 publications

(16 citation statements)

References 39 publications

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“…The synthesis of compounds 1 , 2 and 3 , based on the Wittig reaction [30]–[31], differs from that reported in the literature. NMR experiments were performed using a Varian XL-300 spectrometer, IR spectra were taken with a Shimadzu IR-740 instrument and MS spectra were recorded by an HP5971A/MS detector coupled with HP5890 gas chromatograph.…”

Section: Methodsmentioning

confidence: 82%

Antifungal Activity of Resveratrol against Botrytis cinerea Is Improved Using 2-Furyl Derivatives

et al. 2011

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The antifungal effect of three furyl compounds closely related to resveratrol, (E)-3,4,5-trimethoxy-β-(2-furyl)-styrene (1), (E)-4-methoxy-β-(2-furyl)-styrene (2) and (E)-3,5-dimethoxy-β-(2-furyl)-styrene (3) against Botrytis cinerea was analyzed. The inhibitory effect, at 100 µg ml−1 of compounds 1, 2, 3 and resveratrol on conidia germination, was determined to be about 70%, while at the same concentration pterostilbene (a dimethoxyl derivative of resveratrol) produced complete inhibition. The title compounds were more fungitoxic towards in vitro mycelial growth than resveratrol and pterostilbene. Compound 3 was the most active and a potential explanation of this feature is given using density functional theory (DFT) calculations on the demethoxylation/demethylation process. Compound 3 was further evaluated for its effects on laccase production, oxygen consumption and membrane integrity of B. cinerea. An increase of the laccase activity was observed in the presence of compound 3 and, using Sytox Green nucleic acid stain, it was demonstrated that this compound altered B. cinerea membrane. Finally, compound 3 partially affected conidia respiration.

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Section: Methodsmentioning

confidence: 82%

Antifungal Activity of Resveratrol against Botrytis cinerea Is Improved Using 2-Furyl Derivatives

et al. 2011

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“…The tube was placed in an autoclave, the autoclave purged 3× with hydrogen, and the hydrogen pressure regulated at 1200 psi for 2 d. The inhomogeneous mixture was filtered to remove the catalyst, and the solvent was then removed in vacuo . The resulting solid was recrystallized from EtOH (100 mL), the precipitate collected by filtration, and dried in vacuo to give 7b as a pale yellow solid (1.262 g, 80%). IR (cast film) 3051, 1589, 1482, 1436 cm –1 .…”

Section: Methodsmentioning

confidence: 99%

Incorporation of steroidal biomarkers into petroleum model compounds

Scherer

Hampel

Gray

et al. 2012

J of Physical Organic Chem

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A series of fully‐substituted 5,6‐benzoquinolines covalently fused to the chlolestane framework has been synthesized to serve as model compounds for the poorly characterized components found in the heaviest fractions of petroleum, namely the asphaltenes. Acid‐catalyzed cyclocondensation of an aromatic imine with 5‐α‐cholestan‐3‐one gives 5,6‐benzoquinoline cycloadducts incorporating the steroidal biomarker fused to the benzoquinoline system at the 3,4‐positions, with various pendent substituents in the 2‐position. X‐ray crystallography of three such derivatives shows that the solid‐state geometries of these molecules are quite similar, and packing in the solid state appears to be dominated to a great extent by the nature of the pendent substituent. X‐ray crystallography and solution phase circular dichroism spectroscopy together suggest that the conjugated benzoquinoline moiety adopts a helical conformation. Copyright © 2012 John Wiley & Sons, Ltd.

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“…[7] A diastereomeric mixture of (E)-and (Z)-3,3Ј-dibromostilbene (4) was synthesized by the reaction of 3-bromobenzaldehyde and 3-bromobenzyl bromide under Wittig conditions. [8] This mixture was directly treated with porphy- rin 3 by utilizing copper-free Sonogashira reaction conditions to give tweezer 5 in good yield. [9] Isolation of the (Z) and (E) configurational isomers of tweezer 5 was successfully achieved by using preparative thin-layer chromatography (TLC) with CHCl 3 as the eluent [R f of the (Z) and (E) isomers are 0.78 and 0.59, respectively].…”

Section: Resultsmentioning

confidence: 99%

Configurational Isomers of a Stilbene‐Linked Bis(porphyrin) Tweezer: Synthesis and Fullerene‐Binding Studies

Fathalla

Jayawickramarajah

2009

Eur J Org Chem

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Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis

Cited by 31 publications

References 39 publications

Antifungal Activity of Resveratrol against Botrytis cinerea Is Improved Using 2-Furyl Derivatives

Antifungal Activity of Resveratrol against Botrytis cinerea Is Improved Using 2-Furyl Derivatives

Incorporation of steroidal biomarkers into petroleum model compounds

Configurational Isomers of a Stilbene‐Linked Bis(porphyrin) Tweezer: Synthesis and Fullerene‐Binding Studies

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