Organic Selenium Compounds. XVIII. On the Existence of Monoselenocarboxylic Acids.

Jensen, Kai Arne; Bøje, Lars; Henriksen, Lars; Liaaen‐Jensen, S.; Svensson, Sigfrid

doi:10.3891/acta.chem.scand.26-1465

Cited by 31 publications

(2 citation statements)

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“…Protocols for synthesizing diacyldiselenides have been reported (Niyomura et al 1999;Nishiyama et al 1989;Ishihara and Kato 1972;Jensen et al 1972;Koketsu et al 2002). These methods have certain adverse like the slender availability of the precursor, use of swank reagents and the multiple steps for preparation.…”

Section: Introductionmentioning

confidence: 99%

Peptide Bond Formation via Nα-Protected Diacyldiselenides

Vathsala

Kumar

Sagar

et al. 2018

Int J Pept Res Ther

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A simple, straightforward, for the peptide bond formation employing corresponding carboxylic acids and amines derived from amino acids via N α -protected diacyldiselenide is delineated. The key step of the synthesis is the in situ generation of N α -protected diacyldiselenide using NaBH 2 Se 3 as selenating reagent, followed by trapping with an amino acid ester leading to the peptide. The formation of N α -protected diacyldiselenide was confirmed through TLC and HRMS analysis using crude sample. The reaction is clean and all the products were obtained in moderate to good yields, including for sterically hindered amino acids. The protocol is free from racemisation, compatible with Fmoc, Cbz and Boc groups.

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Section: Introductionmentioning

confidence: 99%

Peptide Bond Formation via Nα-Protected Diacyldiselenides

Vathsala

Kumar

Sagar

et al. 2018

Int J Pept Res Ther

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“…In fact, though several arom atic bis(acyl) selenides have b een isolated as crystals [1]. O nly one aliphatic d e rivative has been described by Jensen and H endriksen w ho isolated bis(ethanecarbonyl) selenide in low yield from the reaction of propanoyl chloride with hydrogen selenide [2], In the course of our studies concerning selenocarboxylic acid derivatives, a series of aliphatic bis(acyl) selenides w ere required. H erein we wish to re p o rt the isolation and characterization of sim ple aliphatic bis(acyl) selenides 1 .…”

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confidence: 99%

Aliphatic Bis(acyl) Selenides — Synthesis and Characterization

Kageyama

Tsutsumi

Murai

et al. 1989

Zeitschrift Für Naturforschung B

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Bis(acyl) Selenide, Carboxylic Acid Selenoanhydride A series of aliphatic bis(acyl) selenides 1 were isolated from the reaction of acyl chlorides with sodium selenide and characterized.In gen eral, the chalcogeno isologues of aliphatic carboxylic acid derivatives are less stable than the arom atic ones therm ally and tow ards oxygen. In fact, though several arom atic bis(acyl) selenides have b een isolated as crystals [1]. O nly one aliphatic d e rivative has been described by Jensen and H endriksen w ho isolated bis(ethanecarbonyl) selenide in low yield from the reaction of propanoyl chloride with hydrogen selenide [2], In the course of our studies concerning selenocarboxylic acid derivatives, a series of aliphatic bis(acyl) selenides w ere required. H erein we wish to re p o rt the isolation and characterization of sim ple aliphatic bis(acyl) selenides 1 .A series of aliphatic bis(acyl) selenides 1 were iso lated in good yields from the reaction of sodium selenide w ith tw o equivalents of acyl chloride in e th e r (eq. (1)). F or exam ple, a solution of propanoyl chloride (22 m m ol) in e th e r (10 ml) was added to sodium selenide (11 m m ol) and the m ixture was stir red at 15 °C for 10 h. T he precipitates was rem oved by filtration and the solvent was evap o rated under reduced p ressure. D istillation of the residue in vacuo afforded 84% of bis(ethanecarbonyl) selenide l b . Sim ilarly, the reaction w ith o th e r acyl chlorides af

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