First direct synthesis of 3-hydroxy-pent-4-ynoic acids. Application to the synthesis of pyran-2-ones

López‐Reyes, Morelia E.; López‐Cortés, José G.; Ortega‐Alfaro, M. Carmen; Toscano, Rubén A.; Álvarez-Toledano, Cecilio

doi:10.1016/j.tet.2013.06.069

Cited by 14 publications

(6 citation statements)

References 41 publications

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“…MgPc (Sigma-Aldrich, Saint Louis, MO, USA) and Nylon 11 (Sigma-Aldrich, Saint Louis, MO, USA) ( Figure 1 a,c) were obtained from commercial sources, without purification prior to their use. The powders for the allene C 24 H 26 O 5 ( Figure 1 b) were synthesized using the procedure reported previously by some authors [ 31 , 32 ]. The semiconductor membranes were manufactured from the following steps: (i) doping and characterization of MgPc; (ii) deposit of consecutive layers of Nylon 11 polymer matrix and doped MgPc; (iii) thermal relaxation treatment, for the incorporation of semiconductor particles in the membrane matrix; and (iv) structural characterization.…”

Section: Methodsmentioning

confidence: 99%

New Development of Membrane Base Optoelectronic Devices

et al. 2017

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It is known that one factor that affects the operation of optoelectronic devices is the effective protection of the semiconductor materials against environmental conditions. The permeation of atmospheric oxygen and water molecules into the device structure induces degradation of the electrodes and the semiconductor. As a result, in this communication we report the fabrication of semiconductor membranes consisting of Magnesium Phthalocyanine-allene (MgPc-allene) particles dispersed in Nylon 11 films. These membranes combine polymer properties with organic semiconductors properties and also provide a barrier effect for the atmospheric gas molecules. They were prepared by high vacuum evaporation and followed by thermal relaxation technique. For the characterization of the obtained membranes, Fourier-transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), and energy dispersive spectroscopy (EDS) were used to determine the chemical and microstructural properties. UV-ViS, null ellipsometry, and visible photoluminescence (PL) at room temperature were used to characterize the optoelectronic properties. These results were compared with those obtained for the organic semiconductors: MgPc-allene thin films. Additionally, semiconductor membranes devices have been prepared, and a study of the device electronic transport properties was conducted by measuring electrical current density-voltage (J-V) characteristics by four point probes with different wavelengths. The resistance properties against different environmental molecules are enhanced, maintaining their semiconductor functionality that makes them candidates for optoelectronic applications.

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Section: Methodsmentioning

confidence: 99%

New Development of Membrane Base Optoelectronic Devices

et al. 2017

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“…In a previous communication, when 100 was treated with NBS in acetonitrile 5‐bromo‐3,4‐dihydro‐2 H ‐pyran‐2‐ones 103 (6‐ endo ‐ dig products) were selectively formed …”

Section: Reactions Involving Other Activating Agentsmentioning

confidence: 92%

“…Alkynones such as 95 , for example, were used to prepare β‐hydroxyacid derivatives 96 as synthons for producing 2 H ‐pyran‐2‐one derivatives. So, as shown in Scheme , we obtained β‐hydroxyacids by a direct method promoted by BF 3 · Et 2 O with the use of different bis(trimethylsilyl)ketene acetals, with the ultimate formation of dehydration/decarboxylation byproducts 97 and dehydration/rearrangement byproducts 98 …”

Section: Reactions Involving Other Activating Agentsmentioning

confidence: 99%

Reactions of Bis(trimethylsilyl)ketene Acetals with Several Activated Organic Substrates

Toledano

Penieres‐Carrillo

2018

Eur J Org Chem

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“…[8] Recently,w er eported the direct synthesis of these highly functionalized compounds through the nucleophilic addition of bis-(trimethylsilyl)ketene acetals to propargyl ketones activated by BF 3 ·Et 2 O. [9] We showed that b-hydroxy-g-alkynoic acids can react regioselectively with N-bromosuccinimide to give 5-bromo-3,4-dihydro-2 H-pyran-2-ones 3 (6-endo-dig product, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%