%0 Journal Article %1 ISI:000284064100004 %A Sabounchei, Seyyed Javad %A Shahriary, Parisa %A Nojini, Zabiholla Bolboli %A Khavasi, Hamid Reza %A Arici, Cengiz %A Dal, Hakan %C 111 RIVER ST, HOBOKEN, NJ 07030 USA %D 2010 %I JOHN WILEY & SONS INC %J HETEROATOM CHEMISTRY %K imported %N 7 %P 475-485 %R 10.1002/hc.20633 %T Synthesis of New Phosphorus Ylides: Spectroscopic and X-ray Structural Studies %V 21 %X Stable phosphoranes, Ar(3)P = CHCOR (R = C(6)H(5), C(6)H(4)NO(2), C(6)H(4)OCH(3), CH 3, OCH(2)C(6)H(5); Ar = p-tolyl or phenyl), have been C-acylated by acetic anhydride to obtain new types of phosphorus ylides. Synthesis and characterization of six phosphorus ylides of the type Ar(3)PC(COCH(3))(COR) are reported. The reaction of \(p-tolyl)(3)PCHCOC(6)H(5)\ (I),\(p-tolyl)(3)PCHCOC(6)H(4)NO(2)\ (II), \Ph(3)PCHCOC(6)H(4)NO(2)\ (III), \Ph(3)PCHCOC(6)H(4)OCH(3)\ (IV), \(p-tolyl)(3)PCHCOCH(3)\ (V), and \Ph(3)PCHCOOCH(2)C(6)H(5)\ (VI) with acetic anhydride in dry chloroform as solvent gives (ptolyl)(3)PC(COMe)(COC(6)H(5)), alpha-acetyl-alpha-benzoylmethylenetriphenylphosphorane (1), \(p-tolyl)(3)PC(COMe)(COC(6)H(4)NO(2))\ (2), \Ph(3)PC(COMe)(COC(6)H(4)NO(2))\ (3), \Ph(3)PC(COMe)(COC(6)H(4)OCH(3))\ (4), \(p-tolyl)(3)PC(COCH(3))(2)\ (5), and \Ph(3)PC(COMe)(COOCH(2)C(6)H(5))\ (6). Single crystal X-ray analyses for ylides 2, 5, and 6 reveal the monoclinic (2, 5) and triclinic (6) crystal systems. Characterization of the obtained compounds was also performed by elemental analysis, IR, (1)H, (31)P, and (13)C NMR. The geometries of these compounds have been investigated using density functional theory (DFT). In addition, electronic parameters of these compounds such as HOMO and LUMO energy, Mulliken partial charge, and dipole moment were obtained. In this paper, the reactivity of these ylides is discussed in regard to the aforementioned data. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:475-485, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20633

@article{ISI:000284064100004, abstract = {{Stable phosphoranes, Ar(3)P = CHCOR (R = C(6)H(5), C(6)H(4)NO(2), C(6)H(4)OCH(3), CH 3, OCH(2)C(6)H(5); Ar = p-tolyl or phenyl), have been C-acylated by acetic anhydride to obtain new types of phosphorus ylides. Synthesis and characterization of six phosphorus ylides of the type Ar(3)PC(COCH(3))(COR) are reported. The reaction of \{(p-tolyl)(3)PCHCOC(6)H(5)\} (I),\{(p-tolyl)(3)PCHCOC(6)H(4)NO(2)\} (II), \{Ph(3)PCHCOC(6)H(4)NO(2)\} (III), \{Ph(3)PCHCOC(6)H(4)OCH(3)\} (IV), \{(p-tolyl)(3)PCHCOCH(3)\} (V), and \{Ph(3)PCHCOOCH(2)C(6)H(5)\} (VI) with acetic anhydride in dry chloroform as solvent gives (ptolyl)(3)PC(COMe)(COC(6)H(5)), alpha-acetyl-alpha-benzoylmethylenetriphenylphosphorane (1), \{(p-tolyl)(3)PC(COMe)(COC(6)H(4)NO(2))\} (2), \{Ph(3)PC(COMe)(COC(6)H(4)NO(2))\} (3), \{Ph(3)PC(COMe)(COC(6)H(4)OCH(3))\} (4), \{(p-tolyl)(3)PC(COCH(3))(2)\} (5), and \{Ph(3)PC(COMe)(COOCH(2)C(6)H(5))\} (6). Single crystal X-ray analyses for ylides 2, 5, and 6 reveal the monoclinic (2, 5) and triclinic (6) crystal systems. Characterization of the obtained compounds was also performed by elemental analysis, IR, (1)H, (31)P, and (13)C NMR. The geometries of these compounds have been investigated using density functional theory (DFT). In addition, electronic parameters of these compounds such as HOMO and LUMO energy, Mulliken partial charge, and dipole moment were obtained. In this paper, the reactivity of these ylides is discussed in regard to the aforementioned data. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:475-485, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20633}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{111 RIVER ST, HOBOKEN, NJ 07030 USA}}, affiliation = {{Sabounchei, SJ (Reprint Author), Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran. Sabounchei, Seyyed Javad; Shahriary, Parisa, Bu Ali Sina Univ, Fac Chem, Hamadan 65174, Iran. Nojini, Zabiholla Bolboli, Shahid Chamran Univ, Fac Sci, Dept Chem, Ahwaz, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran 1983963113, Iran. Arici, Cengiz, TUBITAK, Basic Sci Res Grp, TR-06100 Ankara, Turkey. Dal, Hakan, Anadolu Univ, Dept Chem, TR-26470 Eskisehir, Turkey.}}, author = {Sabounchei, Seyyed Javad and Shahriary, Parisa and Nojini, Zabiholla Bolboli and Khavasi, Hamid Reza and Arici, Cengiz and Dal, Hakan}, author-email = {{Jsabounchei@yahoo.co.uk}}, biburl = {https://www.bibsonomy.org/bibtex/2796920fcb622faf513af6b09843151a6/hkhavasi}, cited-references = {{ALLEN FH, 1987, J CHEM SOC PERK T 2, pS1, DOI 10.1039/p298700000s1. Bachrach S.M., 1994, CHEM ORGANOPHOSPHORU, V3, P273. BART JC, 1969, C J ACTA CRYST B, V25, P762. BART JCJ, 1969, J CHEM SOC B, P350, DOI 10.1039/j29690000350. BESTMANN HJ, 1962, CHEM BER-RECL, V95, P1513, DOI 10.1002/cber.19620950631. Castaneda F, 2005, ACTA CRYSTALLOGR C, V61, pO496, DOI 10.1107/S0108270105015064. Castaneda F, 2003, PHOSPHORUS SULFUR, V178, P1973, DOI 10.1080/10426500390228657. Castaneda F, 2001, ACTA CRYSTALLOGR C, V57, P180, DOI 10.1107/S0108270100016012. Castaneda F, 2007, ACTA CRYSTALLOGR C, V63, pO65, DOI 10.1107/S0108270106051201. CHOPARD PA, 1965, J ORG CHEM, V30, P1015, DOI 10.1021/jo01015a015. COLLINS JB, 1976, J CHEM PHYS, V64, P5142, DOI 10.1063/1.432189. Dunitz J. D., 1979, XRAY ANAL STRUCTURE. Gordon A. J., 1972, CHEM COMPANION, P438. HOWELLS MA, 1973, J AM CHEM SOC, V95, P16. JOHONSON AW, 1993, YLIDES IMINES PHOSPH, P101. KALYANASUNDARI M, 1994, ACTA CRYSTALLOGR C, V50, P1738, DOI 10.1107/S0108270194001137. MARYANOFF BE, 1989, CHEM REV, V89, P863, DOI 10.1021/cr00094a007. PEARSON RG, 1988, INORG CHEM, V27, P734, DOI 10.1021/ic00277a030. Ramazani A, 2000, TETRAHEDRON LETT, V41, P567, DOI 10.1016/S0040-4039(99)02066-3. Sabounchei SJ, 2008, POLYHEDRON, V27, P2015, DOI 10.1016/j.poly.2008.03.009. Sabounchei SJ, 2008, POLYHEDRON, V27, P1963, DOI 10.1016/j.poly.2008.03.010. Sabounchei SJ, 2007, J ORGANOMET CHEM, V692, P5440, DOI 10.1016/j.jorganchem.2007.08.044. Sabounchei SJ, 2007, POLYHEDRON, V26, P2845, DOI 10.1016/j.poly.2007.01.053. Sabounchei SJ, 2007, ACTA CRYSTALLOGR E, V63, pO3160, DOI 10.1107/S1600536807022623. Sabounchei SJ, 2006, PHOSPHORUS SULFUR, V181, P447, DOI 10.1080/104265091001290. Sabounchei S J, 2008, CHIN CHEM SOC, V55, P1. Sheldrick G.M., 1997, SHELX97 PROGRAM CRYS. {[}Anonymous], 2005, X AREA VERS 1 30 PRO. Stoe\&Cie, 2005, X STEP32 VERS 1 07B. WILSON IF, 1972, J CHEM SOC PERK T 1, P31, DOI 10.1039/p19720000031. WITTIG G, 1980, SCIENCE, V210, P600, DOI 10.1126/science.210.4470.600. Yavari I, 1996, SYNTHETIC COMMUN, V26, P4495, DOI 10.1080/00397919608003851. Yavari I, 1997, PHOSPHORUS SULFUR, V130, P73, DOI 10.1080/10426509708033699.}}, doc-delivery-number = {{678HG}}, doi = {{10.1002/hc.20633}}, funding-acknowledgement = {{University of Bu-Ali Sina}}, funding-text = {{Contract grant sponsor: University of Bu-Ali Sina.}}, interhash = {f2b74d2c7a985aa81944a5f1df118c00}, intrahash = {796920fcb622faf513af6b09843151a6}, issn = {{1042-7163}}, journal = {{HETEROATOM CHEMISTRY}}, journal-iso = {{Heteroatom Chem.}}, keywords = {imported}, keywords-plus = {{MERCURY(II) HALIDES; ONE-POT; COMPLEXES}}, language = {{English}}, number = {{7}}, number-of-cited-references = {{33}}, pages = {{475-485}}, publisher = {{JOHN WILEY \& SONS INC}}, research-areas = {{Chemistry}}, times-cited = {{4}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Synthesis of New Phosphorus Ylides: Spectroscopic and X-ray Structural Studies}}, type = {{Article}}, unique-id = {{ISI:000284064100004}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{2}}, volume = {{21}}, web-of-science-categories = {{Chemistry, Multidisciplinary}}, year = {{2010}} }