Phenyl selenide anion, a superior reagent for the SN2 cleavage of esters and lactones

Liotta, Dennis; Sunay, Ustun B.; Santiesteban, Hector; MARKIEWICZ, W.

doi:10.1021/jo00326a001

Cited by 118 publications

(41 citation statements)

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“…The possible mechanism about this transformation is that carboxylic acid ester (4) and Fe (III) first form an adduct (5), then a Cl − from the Fe-complexes (5) attack the adjacent carbon atom of alkoxy group via S N 2 dealkylation, [15] and result to the formation of R 1 COO − (6) and R 2 CH 2 Cl (7) (see Scheme 3), then the protonation of R 1 COO − in the workup stage afford the corresponding carboxylic acid. The formation of the desired 6-chrolo-hexanoic acid (2m) from dealkylation of oxepan-2-one (1p) under Ar atmosphere fur- ther identified this reasonable reaction pathway (Table 3, entry 16).…”

Section: Resultsmentioning

confidence: 99%

An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids

Lian

et al. 2011

Applied Organom Chemis

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A reliable and practical procedure for FeCl 3 -promoted ester cleavage has been developed. Lewis acids including TiCl 4 , ZnO and FeCl 3 etc. were investigated as promoters for O-alkyl cleavage of carboxylic acid ester. Under optimal reaction conditions, FeCl 3 (1.5 equiv.) was found to possess the highest activity and efficiently enhanced dealkylation of aryl esters, alkyl esters and aromatic heterocyclic esters to give their corresponding carboxylic acids in 54-98% yield, the method provides a complementary access to dealkylation of ester under neutral condition.

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Section: Resultsmentioning

confidence: 99%

An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids

Lian

et al. 2011

Applied Organom Chemis

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“…These are usually formed "in situ" from various precursors, for example by reductive cleavage of diselenides [2] or by insertion of selenium into organometallic reagents. [3] Several reducing agents, including LiAlH 4 , NaBH 4 , Na/NH 3 , Bu 3 SnH, have been reported for the preparation of the corresponding metal selenolates under basic as well as neutral conditions.…”

Section: Introductionmentioning

confidence: 99%

Preparation of the First Bench‐Stable Phenyl Selenolate: an Interesting “On Water” Nucleophilic Reagent

et al. 2008

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“…After purification, (S)-3-phenyl-2-(selenophenyl)propan-1-ol, 1 was isolated with an overall yield of 55%. 10,11 It is worth mentioning that the α-selenoalcohol is quite stable and can be stored at 10 °C for more than six months.…”

Section: Enantiomeric Excess Detection With (S)-mentioning

confidence: 99%

Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

Ferreira¹,

Gonçalves²

2010

J. Braz. Chem. Soc.

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Neste artigo demonstramos que o composto (S)-3-fenil-2-(selenofenil)propan-1-ol pode ser empregado com sucesso como agente de derivatização quiral na determinação de excesso enantiomérico de substratos ácidos carboxílicos quirais via RMN de 77 Se. Os derivados diastereoméricos são obtidos através da mistura do agente de derivatização quiral com um substrato ácido não racêmico no próprio tubo de RMN e o excesso enantiomérico é determinado com apenas um espectro. Os melhores resultados foram os obtidos com o emprego do (S)-3-fenil-2-(selenofenil)propan-1-ol, que apresentou boas anisocronias para os sinais de selênio, variando entre Dd = 22 Hz a Dd = 211 Hz, mesmo com até 5 ligações separando o estereocentro do átomo de selênio.In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77 Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2-(selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Dd = 22 Hz to Dd = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.

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Phenyl selenide anion, a superior reagent for the SN2 cleavage of esters and lactones

Cited by 118 publications

References 1 publication

An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids

An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids

Preparation of the First Bench‐Stable Phenyl Selenolate: an Interesting “On Water” Nucleophilic Reagent

Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

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Phenyl selenide anion, a superior reagent for the SN2 cleavage of esters and lactones

Cited by 118 publications

References 1 publication

An efficient FeCl3‐promoted O‐alkyl cleavage of esters to carboxylic acids

An efficient FeCl3‐promoted O‐alkyl cleavage of esters to carboxylic acids

Preparation of the First Bench‐Stable Phenyl Selenolate: an Interesting “On Water” Nucleophilic Reagent

Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

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An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids

An efficient FeCl₃‐promoted O‐alkyl cleavage of esters to carboxylic acids