Highly stereoselective construction of functionalized cyclopropanes from the reaction between acetylenic esters and C–H acids in the presence of triphenylarsine

Maghsoodlou, Malek Taher; Habibi‐Khorassani, Sayyed Mostafa; Heydari, Reza; Charati, Faramarz Rostami; Hazeri, Nourallah; Lashkari, Mojtaba; Rostamizadeh, Mohsen; Marandi, Ghasem; Sobolev, Alexandre N.; Makha, Mohamed

doi:10.1016/j.tetlet.2009.05.051

Cited by 32 publications

(19 citation statements)

References 62 publications

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“…The synthesis and application of multisubstituted cyclopropanes have been subjects of greati nterestb ecause of ther oles of cycloprapanes as basic structural elements in awide rangeofbiologicallya ctivec ompounds andi mportant intermediates in organic synthesis [1][2][3]. As part of our work, we report the synthesis and crystal structure of the title compound.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1- dicarbonitrile, C19H14N2O

Yanping

2015

Zeitschrift Für Kristallographie - New Crystal Structures

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C 19 H 14 N 2 O, triclinic, P1 (no.2), a =8.138(2) Å, b =10.434(2)Å,c=11.109(2)Å,a=99.678(5)°, b =111.028(4)°, g =112.769(5)°, V =758.5 Å 3 , Z =2, Source of materialAmixture of triphenylarsine (0.167 g, 0.15 mmol), phenacyl bromide (0.238 g, 1.2m mol), 2-(4-methylbenzylidene)malononitrile (1 mmol),and NaHCO 3 (0.240 g, 3mmol) wasstirred in CH 3 CN at room temperature. The progress of reaction was monitored by thin-layer chromatography (TLC). Afterc ompletion, water was added and the product was extracted with ethyl acetate. Theo rganic layerw as separated, driedo vera nhydrous sodium sulfate, andthe solventwas evaporated underreduced pressure to afford thec rude product. Colourless crystalso ft he titlec ompound, suitable for X-ray analysis, were obtained by recrystallizing from amixture of methylene chloride and ethylacetate at room temperature. Experimental detailsThe hydrogen atoms were located by geometrically calculations, andtheir positionsand thermal parameters were fixed during the structurerefinement. DiscussionThe synthesis and application of multisubstituted cyclopropanes have been subjects of greati nterestb ecause of ther oles of cycloprapanes as basic structural elements in awide rangeofbiologicallya ctivec ompounds andi mportant intermediates in organic synthesis [1-3]. As part of our work, we report the synthesis and crystal structure of the title compound. Within the crystal structure, thegeometricparameters of cyclopropane arein theu sual ranges.T he C8-C9a nd C9-C10 bond lengthsa re 1.542(2),1 .544(2) Å, respectively. TheC8-C10 bond length is 1.489(2), slightly shorter than the two other C-C bonds. The bond angleso fC 9-C8-C10, C8-C9-C10 and C8-C10-C9a re 61.22(10)°, 57.68(10)°and 61.1(9)°,only slightly deviating from the ideal 60°angle. By analogy with th E-, Z-nomenclature the compound has an E configuration at the C8-C10 unit.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1- dicarbonitrile, C19H14N2O

Yanping

2015

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The synthesis and application of multisubstituted cyclopropanes have been subjects of greati nterestb ecause of ther oles of cycloprapanesasbasic structural elements in awide rangeofbiologicallya ctivec ompounds and important intermediates in organic synthesis [1][2][3]. As part of our work, we report the synthesis and crystal structure of the title compound.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1- dicarbonitrile, C18H11ClN2O

Yanping

2014

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialAmixture of triphenylarsine (0.167 g, 0.15 mmol), phenacyl bromide (0.238 g, 1.2mmol), 2-(4-chlorobenzylidene)malononitrile (1 mmol), and NaHCO 3 (0.240 g, 3mmol) was stirred in CH 3 CN at room temperature. The progress of the reaction was monitored by thin-layer chromatography (TLC). Afterc ompletion, water was added and the product was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to afford the crude product. Colourless crystals of the title compound, suitablefor X-rayanalysis were obtained by recrystallizingfrom amixture of methylene chloride and ethylacetateatroom temperature. Experimental detailsThe hydrogen atoms were located by geometrically calculations, andtheir positionsand thermal parameters were fixed during the structurerefinement. DiscussionThe synthesis and application of multisubstituted cyclopropanes have been subjects of greati nterestb ecause of ther oles of cycloprapanesasbasic structural elements in awide rangeofbiologicallya ctivec ompounds and important intermediates in organic synthesis [1-3]. As part of our work, we report the synthesis and crystal structure of the title compound. Within the crystal structure, theg eometricp arameters of cyclopropane arei nt he usual ranges. The C8-C10, and C9-C10 bond lengths are 1.550(2), 1.544(2) Å, respectively. TheC 8-C9 bond length is 1.492(2), slightly shorter than the other two C-C bonds. The bond angles of C9-C8-C10, C8-C9-C10a nd C8-C10-C9a re 60.96(10)°, 61.40(10)°and 57.64(9)°, showing the angles of ca. 60°the benzoyl and aryl groups are situated in an "E" configuration at the cyclopropane ring.

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“…The synthesis and application of multisubstituted cyclopropanes have been subjects of interest because of the roles of cyclopropanes as basic structural elements in a wide range of biologically active compounds and important intermediates in organic synthesis [1][2][3]. We have been interested in the this type of derivatives and reported several crystallographic analyses of the products.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-benzoyl-3-(4-fluorophenyl)cyclopropane-1,1-dicarbonitrile, C₁₈H₁₁FN₂O

Yang

2016

Zeitschrift Für Kristallographie - New Crystal Structures

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Highly stereoselective construction of functionalized cyclopropanes from the reaction between acetylenic esters and C–H acids in the presence of triphenylarsine

Cited by 32 publications

References 62 publications

Crystal structure of 2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1- dicarbonitrile, C19H14N2O

Crystal structure of 2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1- dicarbonitrile, C19H14N2O

Crystal structure of 2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1- dicarbonitrile, C18H11ClN2O

Crystal structure of 2-benzoyl-3-(4-fluorophenyl)cyclopropane-1,1-dicarbonitrile, C₁₈H₁₁FN₂O

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Highly stereoselective construction of functionalized cyclopropanes from the reaction between acetylenic esters and C–H acids in the presence of triphenylarsine

Cited by 32 publications

References 62 publications

Crystal structure of 2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1- dicarbonitrile, C19H14N2O

Crystal structure of 2-benzoyl-3-(4-methylphenyl)cyclopropane-1,1- dicarbonitrile, C19H14N2O

Crystal structure of 2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1- dicarbonitrile, C18H11ClN2O

Crystal structure of 2-benzoyl-3-(4-fluorophenyl)cyclopropane-1,1-dicarbonitrile, C18H11FN2O

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Crystal structure of 2-benzoyl-3-(4-fluorophenyl)cyclopropane-1,1-dicarbonitrile, C₁₈H₁₁FN₂O