Heterophosphacyclanes in organic synthesis

Черкасов, Р. А.; Пудовик, М. А.

doi:10.1070/rc1994v063n12abeh000132

Cited by 88 publications

(32 citation statements)

References 129 publications

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“…The phosphorus ylides represent an outstanding achievement of the chemistry of the twentieth century [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. The development of the modern chemistry of natural and physiologically active compounds would have been impossible without the phosphorus ylides [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

“…The development of the modern chemistry of natural and physiologically active compounds would have been impossible without the phosphorus ylides [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. They have found use in a wide variety of reactions of interest to synthetic chemists [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Phosphorus ylides are important reagents in synthetic organic chemistry [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16], especially in the synthesis of naturally occurring products, compounds with biological and pharmacological activity [6].…”

Section: Introductionmentioning

confidence: 99%

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<b>Vinyltriphenylphosphonium salt-mediated preparation of thiophene-containing electron-poor alkenes from acetylenic esters, 2-thienylmethanol and triphenylphosphine</b>

Shajari

Ramazani

Ahmadi

2011

Bull. Chem. Soc. Eth.

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ABSTRACT ABSTRACT. Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and alkyl acetylenecarboxylates (methyl acetylenecarboxylate, ethyl acetylenecarboxylate and ethyl phenylacetylenecarboxylate) by 2-thienylmethanol leads to vinyltriphenylphosphonium salts, which undergo an addition-elimination reaction in CH2Cl2 at room temperature to produce the corresponding O-vinylated alkenes via thiophene-containing phosphorus ylides intermediates in fairly high yields. The structural analysis of all products indicated that the reactions are regio-and stereoselective. KEY WORDS KEY WORDS KEY WORDS

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

<b>Vinyltriphenylphosphonium salt-mediated preparation of thiophene-containing electron-poor alkenes from acetylenic esters, 2-thienylmethanol and triphenylphosphine</b>

Shajari

Ramazani

Ahmadi

2011

Bull. Chem. Soc. Eth.

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“…1 Phosphorus ylides are reactive systems, which take part in many valuable reactions in organic synthesis [2][3][4][5][6][7][8][9][10][11][12] and are most often the present work was undertaken for generation of stable phosphoranes. Accordingly, the reaction of triphenylphosphine 1 with dialkylacetylene dicarboxylates 2 (2a or 2b) in the presence of a NH-acid 3 led to the corresponding stable heterocyclic phosphorus ylides 4 (4a or 4b) in excellent yields (see Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of stable phosphorus ylides from 3, 5-dimethylpyrazole and kinetic investigation of the reactions by UV spectrophotometry

Habibi‐Khorassani¹,

Maghsoodlou²,

Nassiri³

et al. 2007

Arkivoc

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Stable crystalline phosphorus ylides were obtained in excellent yields from the 1:1:1 addition reactions between triphenylphosphine and dialkyl acetylenedicarboxylates, in the presence of a NH-acid, such as 3,5-dimethylpyrazole. These stable ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group. To determine the kinetic parameters of the reactions, they were monitored by UV spectrophotometery. The second order fits were drawn and the values of the second order rate constant (k 2 ) were calculated automatically using standard equations within the program. At the temperature range studied, the dependence of the second order rate constant (Ln k 2 ) on reciprocal temperature was in good agreement with the Arrhenius equation. This provided the relevant plots to calculate the activation energy of all reactions. Furthermore, useful information was obtained from studies of the effect of solvent, structure of reactants (different alkyl groups within the dialkyl acetylenedicarboxylates) and also concentration of reactants on the rate of reactions. The proposed mechanism was confirmed according to the obtained results and steady state approximation and first step (k 2 ) of reaction was recognized as a rate-determining step on the basis of experimental data.

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“…It is known that the reaction of acetylenic esters and Ph 3 P produces the carbene-ylide intermediate 2 which is sufficiently stabilized by resonance 10,11 . Thus, compounds 4a-d are apparently obtained from the initial addition of triphenylphosphine as a good nucleophile [12][13][14][15][16] to acetylenic esters as a…”

Section: Introductionmentioning

confidence: 99%

A facile one-pot method for preparation of succinic esters containing several functional groups

Hassani¹,

Islami²,

Sheibani³

et al. 2006

Arkivoc

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Heterophosphacyclanes in organic synthesis

Cited by 88 publications

References 129 publications

<b>Vinyltriphenylphosphonium salt-mediated preparation of thiophene-containing electron-poor alkenes from acetylenic esters, 2-thienylmethanol and triphenylphosphine</b>

<b>Vinyltriphenylphosphonium salt-mediated preparation of thiophene-containing electron-poor alkenes from acetylenic esters, 2-thienylmethanol and triphenylphosphine</b>

Synthesis of stable phosphorus ylides from 3, 5-dimethylpyrazole and kinetic investigation of the reactions by UV spectrophotometry

A facile one-pot method for preparation of succinic esters containing several functional groups

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