An Efficient Synthesis of Stable Phosphorus Ylides Derived from Hydantoin and 5,5-dialkylhydantoins

Yavari, Issa; Zabarjad‐Shiraz, Nader; Maghsoodlou, Malek Taher; Hazeri, Nourallah

doi:10.1080/10426500210660

Cited by 29 publications

(5 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction of the 1:1 triphenylphosphine-dialkyl acetylenedicarboxylate adducts with N-H acids such as imidazole, benzimidazole, benzotriazole [70], 2-aminobenzimidazole [71], indole, 2-acetylpyrrole [72], hydantoin [73], 2-hydroxy benzimidazole [74], 2-aminothiazole [75], harman and harmin [76], 2-benzoxazolinone [77], trifluoroacetamide [78], acetylated acetaminophen [79], N-substituted aryl hydrazine [80], and 1,2-phenylenediamine [81] have provided new stabilized phosphorus ylides.…”

Section: Reaction Of Triphenylphosphine Dialkyl Acetylenedicarboxylamentioning

confidence: 99%

Synthesis and Reactions of Stabilized Phosphorus Ylides

Ramazani

Kazemizadeh

Ahmadi³

et al. 2008

COC

107

View full text Add to dashboard Cite

Stabilized phosphorus ylides, versatile intermediates in synthetic organic chemistry can be prepared by the novel reaction of dialkyl acetylenedicarboxylates (DAAD), triphenylphosphine (TPP) and acids such as phenols, imides, amides, enols, oximes and alcohols. The reaction involves an intermediate formed by the 1:1 conjugate addition reaction of the TPP to DAAD and concomitant protonation of the intermediate by an acid leads to vinyltriphenylphosphonium salts. The salts are unstable intermediates and converted to stabilized phosphorus ylides via Michael addition reaction. The stabilized phosphorus ylides are able to take part in the normal intramolecular Wittig reactions but they are not generally able to participate in the normal intermolecular Wittig reactions. The intermolecular Wittig reactions of the ylides are observed only with highly electron-poor carbonyl groups such as indane-1,2,3-trione. The ylides are converted to electron-poor alkenes via elimination of TPP in solvent-free conditions. Almost all of the final products are valuable families of compounds. †Dedicated to Professor Issa Yavari on the occasion of his 59th birthday.

show abstract

Section: Reaction Of Triphenylphosphine Dialkyl Acetylenedicarboxylamentioning

confidence: 99%

Synthesis and Reactions of Stabilized Phosphorus Ylides

Ramazani

Kazemizadeh

Ahmadi³

et al. 2008

COC

107

View full text Add to dashboard Cite

show abstract

“…In some cases, subsequent intramolecular Wittig reactions then ensue, or an elimination reaction occurs in which the original phosphine is regenerated, to give the final products. Thus, e.g., new phosphorus ylides have been obtained in excellent yield from the reactions of triphenylphosphine, dimethyl acetylenedicarboxylate and strong NH acids, including pyrroles and indoles, 426 hydantoins, 427 benzimidazoles, 428 saccharin, 429 trifluoroacetamide, 430 phthalimide and succinimide. 431,432 New ylides have also been isolated from the related reactions of triphenylphosphine, dimethyl acetylenedicarboxylate and primary aromatic amines, 433 including various aminophenols, 434 2-aminothiophenol, 435 and o-phenylenediamine.…”

Section: Miscellaneous Methods Of Preparing Phosphinesmentioning

confidence: 98%

Phosphines and Related Tervalent Phosphorus Systems

2006

Organophosphorus Chemistry

View full text Add to dashboard Cite

“…[5][6][7][8][9] Synthesis of phosphonium salts often occurs by reaction between triphenylphosphine and an alkyl halide in the presence of a base, but more recently, there are many reports that triphenylphosphine and acetylenic esters are used for generation of stable phosphonium ylides. [5][6][7][8][9][10][11][12][13][14][15][16][17] We describe in this article an efficient synthetic route for synthesis of stable phosphorus ylides containing sulfonamide in the presence of various solvents. Solvent selection in organic synthesis is one of the major routes for approaching goals.…”

Section: Introductionmentioning

confidence: 99%