Ueber neue organische Phosphorverbindungen II. Phosphazine

Staudinger, H.; Meyer, Jules

doi:10.1002/hlca.19190020163

Cited by 175 publications

(33 citation statements)

References 1 publication

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“…In 1919 Staudinger and Meyer synthesized and correctly characterized triphenylphosphonium diphenylmethylide [16,17]. In the work published in 1921, on the reaction of this ylide with diphenylketene and phenylisocyanate, they found for the first time, the reaction which was to be named the Wittig reaction.…”

Section: Introductionmentioning

confidence: 97%

Synthesis and Reactions of Stabilized Phosphorus Ylides

Ramazani

Kazemizadeh

Ahmadi³

et al. 2008

COC

107

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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.

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Section: Introductionmentioning

confidence: 97%

Synthesis and Reactions of Stabilized Phosphorus Ylides

Ramazani

Kazemizadeh

Ahmadi³

et al. 2008

COC

107

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“…in benzene-d6 results in a similar color change over 5 min as described above, indicating consumption of the dicopper carbene. Two sharp 31 P NMR resonances at d 7.36 and À4.79 ppm signal the presence of the carbene transfer product Ph 3 P@CPh 2[30][31][32] as well as free PPh 3 , respectively. In addition, a broad resonance at d 5.20 ppm indicates the formation of…”

mentioning

confidence: 98%

Electronic structure and electrophilic reactivity of discrete copper diphenylcarbenes

Badiei

Warren

2005

Journal of Organometallic Chemistry

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“…In 1919 Staudinger and Meyer synthesized and correctly characterized triphenylphosphonium diphenylmethylide [28,29]. In work published in 1921, on the reaction of this ylide with diphenylketene and phenylisocyanate, they found for the first time, the reaction which was to be named the Wittig reaction.…”

Section: Introductionmentioning

confidence: 97%

Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications

Ramazani

Kazemizadeh

2011

COC

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Triphenylphosphine (TPP), dialkyl acetylenedicarboxylates (DAAD), and acids such as phenols, imides, amides, enols, oximes and alcohols react with each other via a multicomponent reaction to produce stabilized phosphorus ylides. The reactions take place easily, through formation of intermediate formed by the Michael addition of the triphenylphosphine to dialkyl acetylenedicarboxylates and concomitant protonation of the intermediate by an acid leads to vinyltriphenylphosphonium salts. The salts are unstable intermediates and undergo a subsequent Michael addition leads to stabilized phosphorus ylides. In some cases ylide products are stable, but in other cases they cannot be isolated and appear to occur as intermediates on the pathway to an observed product. The stabilized phosphorus ylides are able to take part in the normal intramolecular Wittig reactions and produce a variety of heterocyclic or carbocyclic compounds, but they are not able to participate in the intermolecular Wittig reactions.

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Ueber neue organische Phosphorverbindungen II. Phosphazine

Cited by 175 publications

References 1 publication

Synthesis and Reactions of Stabilized Phosphorus Ylides

Synthesis and Reactions of Stabilized Phosphorus Ylides

Electronic structure and electrophilic reactivity of discrete copper diphenylcarbenes

Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications

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