Phosphorylated aldehydes: Preparations and synthetic uses

Iorga, Bogdan I.; Eymery, Frédéric; Mouriès, Virginie; Savignac, Philippe

doi:10.1016/s0040-4020(98)00896-5

Cited by 51 publications

(16 citation statements)

References 190 publications

(128 reference statements)

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“…[10] The elongation unit 2 carriesa ni mine based Wittig-Horner reagent [11] to construct the first strand and am asked aldehyde( protected as diethyla cetal) as the buildingb lock of the second strand. Due to their efficiency in olefin synthesis, the Wittig-Horner reaction and aK noevenagel condensation were chosen to constructt he two strandso fp olyenei n the two stages.…”

Section: Resultsmentioning

confidence: 99%

“…According to the analysis, the startingc ompound should be as emi-protected phthalaldehyde (as1 ,3-dioxane acetal) as 1. [10] The elongation unit 2 carriesa ni mine based Wittig-Horner reagent [11] to construct the first strand and am asked aldehyde( protected as diethyla cetal) as the buildingb lock of the second strand. ( This compound was synthesized via formylation of diethyl( 3,3-diethoxypropyl)phosphonate followed by imine formation).…”

Section: Resultsmentioning

confidence: 99%

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Template‐Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self‐Assemble into Helical Wires

Pal

Chang

Zeng

et al. 2017

Chemistry A European J

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Pentacene is one of the most versatile organic semiconductors. New synthetic strategies to construct the pentacene skeleton are imperative to produce pentacene derivatives with appropriate solubility, stability, and optoelectronic properties for various applications. This paper describes a template-directed approach to pentacene derivatives. In the retrosynthesis, the acene skeleton is viewed as a laddered double strand polyene instead of the more intuitive linearly fused hexagons. Based on this vision, the template strand of polyene is constructed with Wittig olefination, whereas the second strand is accomplished with Knoevenagel condensation to produce pentacene and tetracene derivatives. The synthetic scheme is flexible enough to generate an array of acene derivatives with substitution patterns that were hitherto difficult to access. Amphiphilic pentacene and tetracene derivatives were also synthesized by the template strategy. One pentacene based amphiphilic rod-coil molecule undergoes self-assembly to form helical wire structures that were visualized with TEM.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Template‐Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self‐Assemble into Helical Wires

Pal

Chang

Zeng

et al. 2017

Chemistry A European J

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“…The versatile WE reaction has numerous applications in the elegant synthesis of intermediates for fine chemicals such as perfumes, fragrances, analgesics, insecticides, carotenoids, pheromones, pharmaceuticals, and prostaglandins and is classically induced by bases under homogeneous [46][47][48][49][50][51] Table 3) [54]. Various magnesium oxide crystals CM-MgO, NA-MgO, NAP-MgO were evaluated in the WE reaction between benzaldehyde and triethylphosphonoacetate to understand the relation between structure and reactivity.…”

Section: Wadsworth-emmons (We) Reactionsmentioning

confidence: 99%

Recent Developments on Catalytic Applications of Nano-Crystalline Magnesium Oxide

Chintareddy

Kantam

2011

Catal Surv Asia

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Nanocrystalline metal oxides, MgO, CuO, ZnO, TiO 2 as catalysts or catalyst supports have been received much attention in the recent years, especially nanocrystalline magnesium oxide (NAP-MgO) has been used as a recyclable catalyst for Wittig, WadsworthEmmons, aza-Michael, Baylis-Hillman, Strecker, Aldol, Claisen-Schmidt condensation and other useful organic reactions. In general, it is reported that nanocrystalline magnesium oxide shows better activity in many organic reactions. These high reactivities are due to high surface areas combined with unusually reactive morphologies. The nanomaterials were also explored as supports to make supported metal catalysts for the organic reactions. The higher activity of these catalysts was studied partly to understand the mechanism of the reaction, the putative reaction pathways were preliminarily presented with the help of spectroscopic support, XPS, silicon, and phosphorus NMR spectroscopy. The catalysts are recovered and reused for several cycles. These catalytic systems are expected to contribute to the development of benign chemical processes.

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“…Phosphorus‐containing aldehydes are advanced reactants for synthetic organic and elementoorganic chemistry . О,О ‐Dialkyl‐ S ‐(1,1‐dimethyl‐2‐oxoethyl)dithiophosphates belong to one of the basic types of phosphorus‐containing aldehydes, where aldehyde fragment is bonded to phosphorus atom through heteroelement (nitrogen, oxygen, and sulfur) (Figure ).…”

Section: Introductionmentioning

confidence: 99%

О,О‐Dialkyl‐S‐(1,1‐dimethyl‐2‐oxoethyl)dithiophosphates: Synthesis and Reactions with n‐Nucleophiles

Газизов

Khairullin

Аксенов

et al. 2015

Heteroatom Chemistry

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Hydrolysis of the new types of iminium salts was used to synthesize О,О‐dialkyl‐S‐(1,1‐dimethyl‐2‐oxoethyl)dithiophosphates or 2‐dialkoxythiophosphorylthio‐substituted aldehydes with carbon isochain. Reactions of aldehydes with N‐, N,N‐, and O,N‐nucleophiles gave new phosphorylated imines containing an acetal group at different positions, perhydro‐1,3‐diazol and oxazol with the diisopropoxythiophosphorylthio group in a side chain, and hydrazone of this aldehyde and diphenylphosphinylacetic acid hydrazide.

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Phosphorylated aldehydes: Preparations and synthetic uses

Cited by 51 publications

References 190 publications

Template‐Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self‐Assemble into Helical Wires

Template‐Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self‐Assemble into Helical Wires

Recent Developments on Catalytic Applications of Nano-Crystalline Magnesium Oxide

О,О‐Dialkyl‐S‐(1,1‐dimethyl‐2‐oxoethyl)dithiophosphates: Synthesis and Reactions with n‐Nucleophiles

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