The solid state conformation of oxo stabilised ylides: X-ray structures of four new polyoxo phosphorus ylides

The first X-ray structure determinations of a trioxo ylide 7, a tetraoxo ylide 8, a tetraoxo bis(ylide) 10 and a hexaoxo bis(ylide) 9 show these compounds to exhibit unexpected effects as regards the relative alignment of the 4–8 contiguous CX units present. Crystal-packing forces are sufficient to over-ride the normal preference for the PC–CO unit in such stabilised ylides to have the syn configuration. A survey of all previous X-ray structures of acyclic oxo-stabilised phosphorus and arsenic ylides is also presented.

[1]  E. Díez-Barra,et al.  Phosphorus ylide niobium complexes; synthesis and characterization of the first α-keto ylide complexes, [{NbCl3(ylide-O,N)}2] and [NbCl3(ylide-O,N) (RCCR′)] (ylide = [{2-thiazolylcarbonyl}methylene]triphenylphosphorane, NOSC4H2CHPPh3). Molecular structure of [NbCl3(NOSC4H2CHPPh3-O,N) (PhCCPr) (Ph = , 1997 .

[2]  Michael A. Beswick,et al.  Platinum-Assisted Addition of Carbonyl-Stabilized Phosphorus Ylides to Pentafluorobenzonitrile and Acetonitrile To Give Platinum(II) Complexes Containing Iminophosphorane and/or N-Bonded β-Imino Phosphorus Ylide Ligands. Crystal and Molecular Structures of trans-[PtCl2{E-NHC(C6F5)C(PPh3)C(O)Me}2] an , 1996 .

[3]  G. Valle,et al.  Reactivity of carbon suboxide toward As and P stabilized ylides. Crystal and molecular structure of CH2{C(=O) [C(=AsPh3) (COOMe)]}2 , 1995 .

[4]  N. Walker,et al.  Synthesis and cytostatic activity of enynes, enediynes and dienediynes linked to intercalators , 1995 .

[5]  M. Hocking,et al.  X-ray structures of triphenylphosphine and 1,2,5-triphenylphosphole products with dimethyl acetylenedicarboxylate tetramer , 1994 .

[6]  G. Valle,et al.  Reactions of C3O2 with Stabilized Triphenylphosphoranes Ph3PCHX (XCN, COMe, COPh) , 1994 .

[7]  Armann Ingolfsson,et al.  Stability and Sensitivity of an EWMA Controller , 1993 .

[8]  Charles P. Quesenberry,et al.  The Effect of Sample Size on Estimated Limits for and X Control Charts , 1993 .

[9]  Fah Fatt Gan,et al.  The run length distribution of a cumulative sum control chart , 1993 .

[10]  J. Macgregor,et al.  The exponentially weighted moving variance , 1993 .

[11]  Emmanuel Yashchin,et al.  Performance of CUSUM control schemes for serially correlated observations , 1993 .

[12]  Layth C. Alwan,et al.  TIME-SERIES INVESTIGATION OF SUBSAMPLE MEAN CHARTS , 1992 .

[13]  S. Bachrach.  Molecular structure of phosphonium ylides , 1992 .

[14]  David M. Rocke.  Xq and Rq charts: Robust control charts , 1992 .

[15]  William H. Woodall,et al.  The effect of autocorrelation on the retrospective X-chart , 1992 .

[16]  Fah Fatt Gan,et al.  An optimal design of CUSUM quality control charts , 1991 .

[17]  Charles P. Quesenberry,et al.  DPV Q charts for start-up processes and short or long runs , 1991 .

[18]  John W. Philpot,et al.  False signal rates for the shewhart control chart with supplementary runs tests , 1991 .

[19]  Douglas C. Montgomery,et al.  Some Statistical Process Control Methods for Autocorrelated Data , 1991 .

[20]  T. Harris,et al.  Statistical process control procedures for correlated observations , 1991 .

[21]  William H. Woodall,et al.  CUSUM charts with variable sampling intervals , 1990 .

[22]  R. Gleiter,et al.  The Structure of Vicinal Pentaketones—X‐Ray Structure Investigations and Calculations , 1990 .

[23]  A. Rheingold,et al.  Phosphorus ylides as hard donor ligands: synthesis and characterization of MCl4(ylide-O)(THF) (M = Ti, Zr, Hf; ylide = (acetylmethylene)triphenylphosphorane, (benzoylmethylene)triphenylphosphorane). Molecular structure of trans-((acetylmethylene)triphenylphosphorane-O)(tetrahydrofuran)tetrachlorotit , 1990 .

[24]  J. Spurrier,et al.  Control charts for detecting cyclical behavior , 1990 .

[25]  Lloyd S. Nelson,et al.  Column: Technical Aids: Monitoring Reduction in Variation with a Range Chart , 1990 .

[26]  G. Bernardinelli,et al.  Trapping and ESR study of an allylic radical involving the participation of a phosphoranyl moiety: R3PC.bul.HCR2 , 1990 .

[27]  C. Cheer,et al.  A phosphorous ylide with a secondary P…O bond. The crystal structure of a-[6-furazano][3,4-b]-quinoxalinyl-a-carbethoxymethylenetriphenylphosphorane(butene-2,3,4-dimethylhexene-3)solvate , 1989 .

[28]  Emmanuel Yashchin,et al.  Weighted Cumulative Sum Technique , 1989 .

[29]  Stephen V. Crowder,et al.  Design of Exponentially Weighted Moving Average Schemes , 1989 .

[30]  David M. Rocke.  Robust control charts , 1989 .

[31]  David C. Hoaglin,et al.  Some Implementations of the Boxplot , 1989 .

[32]  R. M. Norton,et al.  Pocket-Calculator Approximation for Areas under the Standard Normal Curve , 1989 .

[33]  Lloyd S. Nelson,et al.  Calculation of New Limits for X, R Charts When Subgroup Size is Changed , 1988 .

[34]  B. L. Foote,et al.  Spectral analysis in quality control: a control chart based on the periodogram , 1988 .

[35]  Charles W. Champ,et al.  Exact results for shewhart control charts with supplementary runs rules , 1987 .

[36]  Nicholas M.S. Rock,et al.  ROBUST: An interactive FORTRAN-77 package for exploratory data analysis using parametric, ROBUST and nonparametric location and scale estimates, data transformation , 1987 .

[37]  David C. Hoaglin,et al.  Use of Boxplots for Process Evaluation , 1987 .

[38]  D. Hawkins.  Self‐Starting Cusum Charts for Location and Scale , 1987 .

[39]  W. Qiu,et al.  Studies of applications of organoelement compounds of groups V and VI in organic syntheses. XLVI: Synthesis, reactivity and crystal structure of trifluoroacetylmethylenetriphenylarsorane , 1987 .

[40]  J. Stuart Hunter,et al.  The exponentially weighted moving average , 1986 .

[41]  Charles P. Quesenberry,et al.  Screening Outliers in Normal Process Control Data with Uniform Residuals , 1986 .

[42]  Lonnie C. Vance.  Computer Programs: Average Run Lengths of Cumulative Sum Control Charts for Controlling Normal Means , 1986 .

[43]  Stephen M. Stigler,et al.  Estimating serial correlation by visual inspection of diagnostic plots , 1986 .

[44]  K. Waldmann,et al.  Bounds for the Distribution of the Run Length of One-Sided and Two-Sided CUSUM Quality Control Schemes , 1986 .

[45]  H. Schnering,et al.  Über Reaktionen mit Betainen, 20. Mitt. Synthesen stabiler S-Ylide , 1985 .

[46]  Stephen B. Vardeman,et al.  Average Run Lengths for CUSUM Schemes When Observations Are Exponentially Distributed , 1985 .

[47]  Lloyd S. Nelson,et al.  Interpreting Shewhart X̄ Control Charts , 1985 .

[48]  O. Prakash,et al.  Hypervalent iodine. Mixed iodonium ylides , 1984 .

[49]  H. Schnering,et al.  Über Reaktionen mit Betainen, 17. Mitt. Synthese und Kristallstruktur von Pyridinium-di-trihalogenacyl-methyliden , 1983 .

[50]  Gene H. Golub,et al.  Algorithms for Computing the Sample Variance: Analysis and Recommendations , 1983 .

[51]  K. Peters,et al.  Über Reaktionen mit Betainen, 16. Mitt.: Über Betaine und ihre Beziehungen zu N-Yliden Kristallstruktur von Trimethylammoniumtrifluoracetylmethylid , 1983 .

[52]  Lloyd S. Nelson,et al.  Control Chart for Medians , 1982 .

[53]  Lloyd S. Nelson,et al.  Control Charts for Individual Measurements , 1982 .

[54]  R. J. Rowlands,et al.  Snub‐Nosed V‐Mask Control Schemes , 1982 .

[55]  James M. Lucas,et al.  Combined Shewhart-CUSUM Quality Control Schemes , 1982 .

[56]  R W Edwards,et al.  Internal Analytical Quality Control Using the Cusum Chart and Truncated V-Mask Procedure , 1980, Annals of clinical biochemistry.

[57]  K W Kemp,et al.  Internal quality control of radioimmunoassays: monitoring of error. , 1979, The Journal of endocrinology.

[58]  R. J. Howarth,et al.  Application of a generalized power transformation to geochemical data , 1979 .

[59]  K W Kemp,et al.  Internal quality control of radioimmunoassays. , 1978, The Journal of endocrinology.

[60]  H. Burzlaff,et al.  Die Kristall- und Molekülstruktur des 1,2-Bis(methoxycarbonyl)-3-phenylpropen-2-yliden-1-triphenylphosphoran, C31H27O4P , 1974 .

[61]  I. Karle,et al.  The structure of a crowded zwitterion, [(C6H5)3P+](H3COOC)CC[COOCH3][N(C6H4Cl) (NCN−)], derived from triphenylphosphine , 1972 .

[62]  Edward A. Youngs,et al.  Some Results Relevant to Choice of Sum and Sum-of-Product Algorithms , 1971 .

[63]  L. Horner,et al.  Zur Kenntnis der o-Chinone, 32. Über Konformationsstudien an vicinalen Tetracarbonylverbindungen und über Isomerieerscheinungen bei Formoinen , 1968 .

[64]  A. Speziale,et al.  Reactions of Phosphorus Compounds. XI. Geometry of Phosphorus Ylids , 1965 .

[65]  C. Brown,et al.  The crystal structure of benzil , 1965 .

[66]  W. A. Thompson,et al.  PRECISION OF SIMULTANEOUS MEASUREMENT PROCEDURES , 1963 .

[67]  E. S. Page.  CONTINUOUS INSPECTION SCHEMES , 1954 .

[68]  E R JENNINGS,et al.  The use of control charts in the clinical laboratory. , 1950, American journal of clinical pathology.

[69]  J. Wolfowitz,et al.  On the Theory of Runs with some Applications to Quality Control , 1943 .

[70]  L. H. C. Tippett,et al.  ON THE EXTREME INDIVIDUALS AND THE RANGE OF SAMPLES TAKEN FROM A NORMAL POPULATION , 1925 .

[71]  H. Bestmann,et al.  Crystal structure of 1-methoxycarbonyl-4-oxo-2-methyl-2-pentylidene-triphenylphosphorane, C26H25O3P , 1995 .

[72]  H. Bestmann,et al.  Crystal structure of 1-acyl-4-oxo-hexylidene-triphenylphosphorane, C26H27O2P , 1995 .

[73]  Lloyd S. Nelson,et al.  Shewhart Control Charts with Unequal Subgroup Sizes , 1994 .

[74]  Eamonn Mullins,et al.  Introduction to control charts in the analytical laboratory. Tutorial review , 1994 .

[75]  Kenneth E. Case,et al.  Economic Design of Control Charts: A Literature Review for 1981–1991 , 1994 .

[76]  M. H. Ramsey,et al.  Productivity enhancement in atomic spectroscopy. Appropriate precision: matching analytical precision specifications to the particular application , 1993 .

[77]  J. Fernández-Baeza,et al.  Carbon-fluorine bond cleavage in C6F5X arenes by carbonyl-stabilized phosphorus ylides. Synthesis of Ph3P:C(C6F4X-4)R (X=CN or NO2). Crystal and molecular structure of Ph3P:C(C6F4CN-4)CO2Et , 1993 .

[78]  Philip J Lowthian,et al.  Effectiveness of analytical quality control is related to the subsequent performance of laboratories in proficiency tests , 1993 .

[79]  R. Gleiter,et al.  Synthesis and properties of 4,4,9,9-tetramethyl[12]paracyclophane-5,6,7,8-tetrone , 1992 .

[80]  Johannes Ledolter,et al.  Two Case Studies Involving an Optical Emission Spectrometer , 1992 .

[81]  B W Turnbull,et al.  Optimal checking procedures for monitoring laboratory analyses. , 1992, Statistics in medicine.

[82]  Stephen V. Crowder,et al.  An EWMA for Monitoring a Process Standard Deviation , 1992 .

[83]  A. Abell,et al.  A Single-Crystal X-Ray Analysis of a Novel Intramolecular Hydrogen-Bonded Biphenyl Phosphorane , 1990 .

[84]  D. L. Wilkinson,et al.  Investigation and reinvestigation of the molecular structure of phosphorus ylides , 1989 .

[85]  A. Abell,et al.  Reactions of 4-Methyl-1-(1′-methylethyl)-4-nitrocyclohexa-2,5-dien-1-yl Acetates With Nitrogen Dioxide; Towards a Mechanism for the Formation of Polynitro Cyclohexenyl Esters on Reaction of p-Cymene With Nitrogen Dioxide in Acetic Anhydride , 1989 .

[86]  A. Abell,et al.  A Mechanistic Study of the Wittig Reaction Between a Cyclic Anhydride and a Stabilized Phosphorane , 1988 .

[87]  K. Peters,et al.  Crystal structure of diethyl-methyl-ammonium-trifluoracetyl-methylide-hydrate , 1984 .

[88]  Youqi Tang,et al.  Remarks on the structural evidence of high reactivity of arsonium ylides bearing with an electron-withdrawing substituent , 1982 .

[89]  J. Lucas,et al.  Robust cusum: a robustness study for cusum quality control schemes , 1982 .

[90]  A. White,et al.  The crystal structures of 1,3-Diphenylpropane-1,2,3-trione, 1,4-Diphenylbutane-1,2,3,4-tetraone, 2,4-Dihydroxy-2,5-diphenylfuran-3(2H)-one and 3,3-Dihydroxy- 1,4-diphenylbutane-1,2,4-trione , 1982 .

[91]  R. Howarth,et al.  The frequency distribution of analytical error , 1980 .

[92]  Michael J. Thompson,et al.  Statistical appraisal of interference effects in the determination of trace elements by atomic-absorption spectrophotometry in applied geochemistry , 1979 .

[93]  C. Raston,et al.  Chemistry and crystal structures of 1,3-Bis(4'-bromophenyl)propane- 1,2,3-trione, 3,5-Diphenyl- 1,2-dithiolylium-4-olate and 4-Hydroxy-3,5-diphenyl-1,2-dithiolium perchlorate , 1978 .

[94]  Stephen E. Derenzo,et al.  Approximations for Hand Calculators Using Small Integer Coefficients , 1977 .

[95]  J. Trotter,et al.  The structure of the adduct of Ph3P = N.Ph and MeO2C.C [triple‐bond] C.CO2Me , 1965 .

[96]  S. W. Roberts.  Properties of control chart zone tests , 1958 .