Simple Synthesis of<i>Geminal</i>Diacetates (Acylals) of Aromatic Aldehydes

Jahng, Yurngdong; Rahman, Motiur A. F. M.

doi:10.1080/00397910500514154

Cited by 6 publications

(2 citation statements)

References 49 publications

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“…The N-alkyl 1,2-phenylenediamines were prepared from the reaction of the corresponding commerically available primary amines with 1-fluoro-2-nitrobenzene, followed by reduction with H 2 catalyzed by Pd/C. [24][25][26] Benzo-2,1,3-selenadiazole was prepared by the reaction of 1,2-phenylenediamine with selenium dioxide according to literature. 27 Anhydrous-grade solvents were used without further purification.…”

Section: Materials and General Proceduresmentioning

confidence: 99%

Synthetic, structural, and computational investigations of N-alkyl benzo-2,1,3-selenadiazolium iodides and their supramolecular aggregates

et al. 2016

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Despite their versatility, the application of telluradiazoles as supramolecular building blocks is considerably constrained by their sensitivity to moisture. Albeit more robust, their selenium analogues form weaker supramolecular interactions. These, however, are enhanced when one nitrogen atom is bonded to an alkyl group. Here we investigate general methods for the synthesis of such derivatives. Methyl, iso-propyl and tert-butyl benzo-2,1,3-selenadiazolium cations were prepared by direct alkylation or cyclo-condensation of the alkyl-phenylenediamine with selenous acid. While the former reaction only proceeds with the primary and tertiary alkyl iodides, the latter is very efficient. Difficulties reported in earlier literature are attributable to the formation of adducts of benzoselenadiazole with its alkylated cations and side reactions initiated by aerobic oxidation of iodide. However, the cations themselves are resilient to oxidation and stable in acidic to neutral aqueous medium. X-ray crystallography was used in the identification and characterization of the following compounds: [C6H4N2(R)Se](+)X(-), (R = CH(CH3)2, C(CH3)3; X = I(-), I3(-)], [C6H4N2(CH3)Se](+)I(-), and [C6H4N2Se][C6H4N2(CH3)Se]2I2. Formation of SeN secondary bonding interactions (chalcogen bonds) was only observed in the last structure as anion binding to selenium is a strong competitor. The relative strengths of those forces and the structural preferences they enforce were assessed with DFT-D3 calculations supplemented by AIM analysis of the electron density.

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Section: Materials and General Proceduresmentioning

confidence: 99%

Synthetic, structural, and computational investigations of N-alkyl benzo-2,1,3-selenadiazolium iodides and their supramolecular aggregates

et al. 2016

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“…A practical and more efficient alternative with an inexpensive reagent under solvent‐free condition is of considerable interest. We herein describe a simple and efficient procedure for the preparation of geminal diacylates of aldehydes and examine the scope of such a reaction 21…”

Section: Introductionmentioning

confidence: 99%

Preparation of Geminal Diacylates (Acylals) of Aldehydes – Scope and Reactivity of Aldehydes with Acid Anhydrides

Rahman¹,

Jahng²

2006

Eur J Org Chem

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Formation of Nitriles, Carboxylic Acids, and Derivatives by Oxidation, Substitution, and Addition

Larock

Yao

2017

Comprehensive Organic Transformations

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Alkanes Arenes Alkenes Dienes Alkynes Alkyl Halides Amines Imines and Derivatives Azides Nitro Compounds Nitrothioalkenes Ethers Sulfides Alcohols Diols Amino Alcohols Azido Alcohols Phenols Aldehydes and Derivatives Ketones Hemiacetals and Lactols Acetals Carboxylic Acids Esters Amides Nitriles

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Simple Synthesis ofGeminalDiacetates (Acylals) of Aromatic Aldehydes

Cited by 6 publications

References 49 publications

Synthetic, structural, and computational investigations of N-alkyl benzo-2,1,3-selenadiazolium iodides and their supramolecular aggregates

Synthetic, structural, and computational investigations of N-alkyl benzo-2,1,3-selenadiazolium iodides and their supramolecular aggregates

Preparation of Geminal Diacylates (Acylals) of Aldehydes – Scope and Reactivity of Aldehydes with Acid Anhydrides

Formation of Nitriles, Carboxylic Acids, and Derivatives by Oxidation, Substitution, and Addition

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