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15 Bibliography
Über metallorganische Komplexverbindungen. G. Wittig, Angew. Chem. 62, 231 (1960).
Über Ylide und Ylid-Reaktionen. G. Wittig, Angew. Chem. 63, 15 (1951).
Fortschritte auf dem Gebiet der organischen Aniono-Chemie. G. Wittig, Angew. Chem. 66, 10 (1954).
Synthesen über Stickstoff-ylide und Phosphor-ylene. G. Wittig, Experientia XII, 41 (1956).
Ursprung und Entwicklung in der Chemie der Phosphin-alkylene. G. Wittig, Angew. Chem. 68, 505 (1956).
Komplexbildung und Reaktivität in der metallorganischen Chemie. G. Wittig, Angew. Chem. 70, 65 (1958).
Neuere präparative Methoden der organischen Chemie II. Carbonyl-Olefinierung mit Triphenyl-phosphin-methylenen. Wittig Reaktion. U. Schöllkopf, Angew. Chem. 71, 260 (1959).
Absicht und Zufall in der Chemie der alkalimetallorganischen Verbindungen. G. Wittig, Verhandlungen der Schweiz. Naturforschenden Gesellschaft, Zürich 1964, 19.
Variationen zu einem Thema von Staudinger; ein Beitrag zur Geschichte der phosphororganischen Carbonyl-Olefinierung. G. Wittig, Pure and Appl. Chem. 9, 245 (1964).
The Role of Ate Complexes as Reaction-Determining Intermediates. G. Wittig, Quarterly Reviews, 20, 191 (1966).
Pentacoordination. E. L. Muetterties and R. A. Schunn, Quarterly Reviews, 20, 245 (1966).
De la Chimie du Phosphore Pentavalent. G. Wittig, Bull. Soc. Chim. France, 1966, 1162.
Pseudorotation in the Hydrolysis of Phosphate Esters. F. H. Westheimer, Acc. Chem. Res. 1, 70 (1968).
Stereochemical Aspects of Phosphorus Chemistry. M. J. Gallgher and I. D. Jenkins, Top. Stereochem. 3, 1 (1968).
Hypervalente Moleküle. J. I. Musher, Angew. Chem. 81, 68 (1969); Angew. Chem. Int. Ed. Engl. 8, 54 (1969).
Organometallic Compounds of Arsenic, Antimony and Bismuth. G. O. Doak and L. D. Freedman, Wiley-Interscience, 1970.
The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth. F. G. Mann, Wiley-Interscience, 1970.
Chimie et Stéréochimie de Nouveaux Dérivés du Phosphore Penta et Hexavalent. D. Hellwinkel, Colloques internationaux du Centre National de la Recherche Scientifique, 182, 177 (1970).
Bewegliche Molekülgerüste — Pseudorotation und Turnstilerotation pentakoordinierter Phosphorverbindungen und verwandte Vorgänge. P. Gillespie, P. Hoffmann, H. Klusacek, D. Marquarding, S. Pfohl, F. Ramirez, E. A. Tsolis und I. Ugi, Angew. Chem. 83, 691 (1971); Angew. Chem. Int. Ed. Engl. 10, 687 (1971).
Penta-and Hexaorganophosphorus Compounds. D. Hellwinkel, in Organic Phosphorus Compounds, Ed. by G. M. Kosolapoff and L. Maier, Vol. 3, p. 185, Wiley, 1972.
Hypervalent Organic Derivatives of Tellurium and Selenium. D. Hellwinkel, Annals of the New York Academy of Sciences, 192, 158 (1972).
Dynamic Stereochemistry of Pentacoordinated Phosphorus and Related Elements. R. Luckenbach, Georg Thieme Verlag, Stuttgart, 1973.
The structural Chemistry of Phosphorus. D. E. C. Corbridge, Elsevier, Amsterdam, 1974.
Organo-Phosphorus Stereochemistry, Part 2, P(V) Compounds. Edit. W. E. McEwen, K. Darrell Berlin, Hutchinson and Ross, Inc., Stroudsburg, Pennsylvania, 1975.
Pentaalkyls and Alkylidene Trialkyls of the Group V Elements. H. Schmidbaur, Advances in Organomet. Chem., 14, 205 (1976).
Polycyclic Carbon-Phosphorus Heterocycles. S. D. Venkataramu, G. D. MacDonell, W. R. Purdum, M. El-Deek and K. D. Berlin, Chem. Rev. 77 121 (1977).
Phosphorus Heterocycles (Including some Arsenic and Antimony Heterocycles). M. J. Gallgher in W. L. F. Armarego, Stereochemistry of Heterocyclic Compounds, Part II, p. 339, Wiley, 1977.
Stereochemistry of Penta-and Hexacoordinate Phosphorus Derivatives. W. S. Sheldrick, Top. Curr. Chem. 73, 1 (1978).
Methoden zur Darstellung und Umwandlung von Organo-arsen-, antimon-und wismuth-Verbindungen. S. Samaan in Methoden der Organischen Chemie (Houben-Weyl) Band XIII/8, Thieme Verlag, 1978.
Arsenheterocyclen. A. Tzschach und J. Heinicke, VEB Deutscher Verlag für Grundstoffindustrie Leipzig, 1978.
A Model for Calculating Conformational Energies in Pentacoordinate Phosphorus Compounds. R. R. Holmes, J. Am. Chem. Soc. 100, 433 (1978).
Pentacoordinate Phosphoranes in Synthesis. K. Burger, in Organophosphorus Reagents in Organic Synthesis, Edit. J. I. G. Cadogan, p. 467, Academic Press, London, 1979.
Structure of Cyclic Pentacoordinated Molecules of Main Group Elements. R. R. Holmes, Accounts Chem. Res. 12, 257 (1979).
The Polytopal Rearrangement Phosphorus. F. H. Westheimer in Rearrangements in Ground and Exited States, Vol. 2, p. 229, Ed. P. de Mayo, Academic Press, (1980).
Pentacoordinated Phosphorus Compounds, Spectroscopy and Structure. R. R. Holmes, ACS Monograph No 175, 1981.
References
Cahours, A.: Liebigs Ann. Chem. 122, 329 (1862)
Lachman, A.: Am. Chem. J. 18, 372 (1896)
For early discussions see: Willgerodt, C.: J. Prakt. Chem. 37, 449 (1888); 41, 291, 526 (1890)
Behrend, R.: Ber. Dtsch. Chem. Ges. 23, 454 (1890)
Bischoff, C. A.: ibid. 23, 1967 (1890)
Schlenk, W., Holtz, J.: Ber. Dtsch. Chem. Ges. 49, 603 (1916)
Schlenk, W., Holtz, J.: ibid. 50, 274 (1917)
see also: Werner, A.: Lehrbuch der Stereochemie, Fischer, Jena, 1904, p. 311 and Werner, A.: Neuere Anschauungen auf dem Gebiete der anorg. Chemie, Viehweg + Sohn, Braunschweig 1905, p. 96
Kossel, W.: Ann. Physik [4] 49, 229 (1916)
Lewis, G. N.: J. Amer. Chem. Soc. 38, 762 (1916)
Langmuir, T.: ibid. 41, 868, 892 (1919); 42, 274 (1920)
Staudinger, H., Meyer, J.: Helv. Chim. Acta 2, 608, 619 (1919)
Hager, F. D., Marvel, C. S.: J. Amer. Chem. Soc. 48, 2689 (1926)
Coffman, D. D., Marvel, C. S.: ibid. 51, 3496 (1929)
Staudinger, H., Meyer, J.: Helv. Chim. Acta 2, 612 (1919)
Staudinger, H., Meyer, J.: ibid. 2, 635 (1919)
Friedrich, M. E. P., Marvel, C. S.: J. Amer. Chem. Soc. 52, 376 (1930)
Wittig, G.: Angew. Chem. 53, 241 (1940)
Wittig, G.: Naturwissenschaften 30, 696 (1942)
Wittig, G.: Angew. Chem. 69, 245 (1957); see also: l. c. 16), p. 699, 700
Wittig, G., Pieper, G., Fuhrmann, G.: Ber. Dtsch. Chem. Ges. 73, 1193 (1940)
Wittig, G.: Suomen Kemistilethi A29, 283 (1956)
Wittig, G., Heintzeler, M., Wetterling, M.-H.: Liebigs Ann. Chem. 557, 201 (1947)
Wittig, G., Wetterling, M.-H.: ibid. 557, 193 (1947)
Wittig, G., Felletschin, G.: ibid. 555, 133, Footnote 2, (1944)
Brockway, L. O., Beach, J. Y.: J. Amer. Chem. Soc. 60, 1836 (1938); Rouault, M.: C. R. Hebd. Séances Acad. Sci. 207, 620 (1938)
Wittig, G., Rieber, M.: Liebigs Ann. Chem. 562, 177 (1949); see also: Wittig, G.: Angew. Chem. 63, 15 (1951)
Wittig, G., Rieber, M.: Naturwissenschaften 35, 345 (1948); Liebigs Ann. Chem. 562, 187 (1949)
Razuvaev, G. A., Osanova, N. A., Grigor'eva, I. K.: Izvest. Akad. Nauk SSSR, Ser. Khim. 1969, 2234 (C.A. 72, 31952c (1970))
Razuvaev, G. A., Osanova, N. A.: Dokl. Akad. Nauk. SSSR 104, 552 (1955), (C.A. 50, 11 268c (1956))
Razuvaev, G. A., Osanova, N. A.: Zhur. Obsch. Khim. 26, 2531 (1956), (C.A. 51, 1875b (1957))
Razuvaev, G. A., Osanova, N. A., Shlyapnikova, I. A.: Zhur. Obshch. Khim. 27, 1466 (1957), (C.A. 52, 3715b (1958))
Wittig, G., Clauß, K.: Liebigs Ann. Chem. 577, 26 (1952)
Wittig, G., Clauß, K.: ibid. 578, 136 (1953).
See also: Gilman, H., Yablunky, H. L.: J. Amer. Chem. Soc. 63, 839 (1941) for earlier unsuccessful attempts
Bach, M.: Dissertation, Heidelberg 1968
Hellwinkel, D.: Habilitationsschrift, Heidelberg 1966
Hellwinkel, D., Wünsche, C., Bach, M.: Phosphorus 2, 167 (1973)
Hellwinkel, D., Kilthau, G.: Liebigs Ann. Chem. 705, 66 (1967). This yellow color at low temperature had already been observed by Wittig and Clauß 1.c. 26) p. 142
Wittig, G., Torssell, K.: Acta Chem. Scand. 7, 1293 (1953)
An earlier report on the preparation of dialkyltriphenylphosphoranes by Grignard, V., Savard, J.: C. R. Hebd. Séances Acad. Sci. 192, 592 (1931) could not be reproduced by later workers: Blount, B. K.: J. Chem. Soc. 1931, 1891; 1932, 337; Denney, D. B., Gross, F. J.: J. Org. Chem. 32, 3710 (1967)
Wittig, G., Geissler, G.: Liebigs Ann. Chem. 580, 44 (1953)
Wittig, G.: Pure and Appl. Chem. 9, 245 (1964)
Vedejs, E., Snoble, K. A. J.: J. Amer. Chem. Soc. 95, 5778 (1973)
Scholsser, M. et al.: Chimia 29, 341 (1975)
Vedejs, E., Meier, G. P., Snoble, K. A. J.: J. Amer. Chem. Soc. 103, 2823 (1981)
See also: Schlosser, M., BaTuong, H.: Angew. Chem. 91, 675 (1979); Angew. Chem. Internat. Ed. Engl. 18, 633 (1979)
Giese, B., Schoch, J., Rüchardt, C.: Chem. Ber. 111, 1395 (1978)
Bestmann, H. J.: Pure and Appl. Chem. 52, 771 (1980)
Some selected reviews: Wittig, G.: Angew. Chem. 68, 505 (1956)
Schöllkopf, U.: Angew. Chem. 71, 260 (1959)
Maercker, A.: Org. Reactions 14, 270 (1965)
Johnson, A. W.: Ylid Chemistry, Academic Press, New York 1966
Schlosser, M.: in Korte, F., Zimmer, H., Niedenzu, K.: Methodicum Chimicum, Band 7, p. 529, Thieme Verlag, Stuttgart 1976; Schlosser, M.: Topics in Stereochemistry 5, 1 (1970)
Pommer, H.: Angew. Chem. 89, 437 (1977); Angew. Chem. Internat. Edit. Engl. 16, 423 (1977)
Gosney, I., Rowley, A. G.: in Cadogan, J. I. G.: Organophosphorus Reagents in Organic Synthesis, Academic Press, London 1979, chapter 2, p. 17
Nast, R., Käb, K.: Liebigs Ann. Chem. 706, 75 (1967)
Seyferth, D., Fogel, J., Heeren, J. K.: J. Amer. Chem. Soc. 88, 2207 (1966)
Razuvaev, G. A., Petukhov, G. G., Osanova, N. A.: Dokl. Akad. Nauk SSSR, 104, 733 (1955); (C.A. 50, 11268f (1956))
Razuvaev, G. A., Petukhov, G. G., Osanova, N. A.: Zhur. Obshch. Khim. 29, 2980 (1959); (C. A. 54, 12030e (1960))
ibid. 31, 2350 (1961); (C. A. 56, 3506i (1962))
Kochendoerfer, E.: Dissertation, Heidelberg 1959
Gielen, M.: in Chemical Applications of Graph Theory (ed. Balaban, A. T.) Academic Press, London 1976. Chapter 9, p. 261
Wittig, G., Kochendoerfer, E.: Angew. Chem. 70, 506 (1958); Chem. Ber. 97, 741 (1964)
Mann, F. G., Chaplin, E. J.: J. Chem. Soc. 1937, 527
Hellwinkel, D.: Diplomarbeit, Heidelberg 1960
Wittig, G., Hellwinkel, D.: Angew. Chem. 74, 76 (1962)
Wittig, G., Maercker, A.: Chem. Ber. 97, 747 (1964)
Schlosser, M., Kadibelban, T., Steinhoff, G.: Liebigs Ann. Chem. 743, 25 (1971)
Hellwinkel, D., Lindner, W.: Chem. Ber. 109, 1497 (1976)
see Hoffmann, R., Howell, J. M., Muetterties, E. J.: J. Amer. Chem. Soc. 94, 3047 (1972)
Hall, C. D., Bramblett, J. D., Lin, F. F. S.: J. Amer. Chem. Soc. 94, 9264 (1972)
Howell, J. M.: J. Amer. Chem. Soc. 99, 7447 (1977)
see for example Dewar, M. J. S., Dougherty, R. C.: The PMO Theory of Organic Chemistry, Plenum Press, New York 1975
Hellwinkel, D., Krapp, W.: Chem. Ber. 110, 693 (1977)
Hellwinkel, D., Wilfinger, H. J.: ibid. 103, 1056 (1970)
John, K. P., Schmutzler, R., Sheldrick, W. S.: J. Chem. Soc. Dalton Transact. 1974, 1841, 2466
Munoz, A. et al.: C. R. Acad. Sci. Ser. C 280, 395 (1975)
On apicophilicity see Bone, S., Trippett, S., Whittle, P. J.: J. Chem. Soc. Perkin Transact. 1, 1974, 2125
Buono, G., Llinas, J. R.: J. Amer. Chem. Soc. 103, 4532 (1981)
Hellwinkel, D., Krapp, W.: Chem. Ber. 111, 13 (1978)
For reviews on ate complexes see: Wittig, G.: Quarterly Reviews 20, 191 (1966)
Tochtermann, W.: Angew. Chem. 78, 355 (1966); Angew. Chem. Internat. Ed. Engl. 5, 351 (1966)
Wittig, G., Angew. Chem. 62, 231 (1950)
Hellwinkel, D.: Chem. Ber. 98, 576 (1965)
Schlosser, M., Kadibelban, T., Steinhoff, G.: Angew. Chem. 78, 1018 (1966); Angew. Chem. Internat. Ed. Engl. 5, 969 (1966)
Daniel, H., Paetsch, J.: Chem. Ber. 101, 1451 (1968)
Ross, B. W., Reetz, K. P.: ibid. 107, 2720 (1974)
Wheatley, P. J., Wittig, G.: Proc. Chem. Soc. 1962, 251
Wheatley, P. J.: J. Chem. Soc. 1964, 2206
For a preliminary note see also: Hellwinkel, D.: Angew. Chem. 76, 756 (1964)
Richards, E. M., Tebby, J. C.: J. Chem. Soc. Ç 1970, 1425
Hellwinkel, D.: Chem. Ber. 99, 3628 (1966)
Hellwinkel, D., Mason, S. F.: J. Chem. Soc. B 1970, 640
Hellwinkel, D., Wilfinger, H. J.: Phosphorus 2, 87 (1972)
Berry, R. S.: J. Chem. Phys. 32, 933 (1960)
Gillespie, R. J.: J. Chem. Soc. 1963, 4672
Muetterties, E. L., Mahler, W., Schmutzler, R.: Inorg. Chem. 2, 613 (1963)
Hellwinkel, D.: Chem. Ber. 99, 3660 (1966)
Hellwinkel, D.: ibid. 99, 3642 (1966)
Hellwinkel, D., Krapp, W.: ibid. 112, 292 (1979)
Ugi, I. et al.: Angew. Chem. 82, 766 (1970); Angew. Chem. Internat. Ed. Engl. 9, 729 (1970)
Gillespie, P. et al.: Angew. Chem. 83, 691 (1971); Angew. Chem. Internat. Ed. Engl. 10, 687 (1971)
Altmann, J. A., Yates, K., Csizmadia, I. G.: J. Amer. Chem. Soc. 98, 1450 (1976)
Shih, S. K., Peyerimhoff, S. D., Buenker, R. J.: J. Chem. Soc. Faraday Transact. 2, 75, 379 (1979), and earlier lit. cited therein
Finocchiaro, P., Gust, D., Mislow, K.: J. Amer. Chem. Soc. 95, 8172 (1973); 96, 3198, 3205 (1974)
Hellwinkel, D. et al.: Chem. Ber. 108, 2219 (1975)
Glaser, R., Blount, J. F., Mislow, K.: J. Amer. Chem. Soc. 102, 2777 (1980)
For the first experimental studies see Hellwinkel, D., Melan, M., Degel, C. R.: Tetrahedron 29, 1895 (1973)
Hellwinkel, D.: Angew. Chem. 78, 749 (1966); Angew. Chem. Internat. Ed. Engl. 5, 725 (1966)
Hellwinkel, D.: Chimia 22, 488 (1968)
Hellwinkel, D., Lindner, W., Wilfinger, H. J.: Chem. Ber. 107, 1428 (1974)
Hellwinkel, D., Wilfinger, H. J.: Tetrahedron Letters 1969, 3423
For a critical evaluation of the coalescence temperature method see: Kost, D., Carlson, E. H., Raban, M.: J. Chem. Soc. D 1971, 656
Kost, D., Zeichner, A.: Tetrahedron Letters 1974, 4533
Whitesides, G. M., Eisenhut, M., Bunting, W. M.: J. Amer. Chem. Soc. 96, 5398 (1974)
Whitesides, G. M., Bunting, M.: ibid. 89, 6801 (1967)
Hellwinkel, D., Lindner, W., Schmidt, W.: Chem. Ber. 112, 281 (1979)
Day, R. O., Husebye, S., Holmes, R. R.: Inorg. Chem. 19, 3616 (1980)
Day, R. O., Holmes, R. R.: ibid. 19, 3609 (1980)
Muetterties, E. L., Schunn, R. A.: Quarterly Reviews 20, 245 (1966)
Holmes, R. R., Deiters, J. A.: J. Amer. Chem. Soc. 99, 3318 (1977)
Holmes, R. R.: Accounts Chem. Res. 12, 257 (1979)
Sheldrick, W. S.: Top. Curr. Res. 73, 1 (1978)
Holmes, R. R.: J. Amer. Chem. Soc. 100, 433 (1978)
Luckenbach, R.: Dynamic Stereochemistry of Pentacoordinated Phosphorus and Related Elements, Thieme, Stuttgart 1973
Hamilton, W. C. et al.: J. Amer. Chem. Soc. 95, 6335 (1973)
Carrell, H. L. et al.: J. Amer. Chem. Soc. 97, 38 (1975)
Hellwinkel, D., Schenk, W.: Angew. Chem. 81, 1049 (1969); Angew. Chem. Internat. Ed. Engl. 8, 987 (1969)
Hellwinkel, D., Schenk, W., Blaicher, W.: Chem. Ber. 111, 1798 (1978)
Hellwinkel, D. et al.: Chem. Ber. 113, 1406 (1980)
Heal, H. G.: J. Inorg. Nucl. Chem. 16, 208 (1961)
Hellwinkel, D.: Chem. Ber. 102, 528 (1969)
Hellwinkel, D., Wilfinger, H. J.: Phosphorus 6, 151 (1976)
Hellwinkel, D., Wünsche, C.: J. Chem. Soc. Chem. Commun. 1969, 1412
Hellwinkel, D.: Chem. Ber. 102, 548 (1969)
Rothuis, R., FontFreide, J. J. H. M., Buck, H. M.: Rec. Trav. Chim. Pays Bas 92, 1308 (1973)
see also Rothuis, R. et al.: Rec. Trac. Chim. Pays Bas 93, 128 (1974)
and van Dijk, J. M. F., Pennings, J. F. M., Buck, H. M.: J. Amer. Chem. Soc. 97, 4836 (1975)
Hellwinkel, D., Wilfinger, H. J.: Liebigs Ann. Chem. 742, 163 (1972)
Rothuis, R., Luderer, T. K. J., Buck, H. M.: Rec. Trav. Chim. Pays Bas 91, 836 (1972)
For a recent review on the role of ion pairs in carbanion chemistry see Hogen-Esch, T. E.: Adv. Phys. Org. Chem. 15, 154 (1977)
Wittig, G., Maercker, A.: J. Organomet. Chem. 8, 491 (1967)
see also Kyba, E. P.: J. Amer. Chem. Soc. 98, 4805 (1976)
Musher, J. I.: Angew. Chem. 81, 68 (1969; Angew. Chem. Internat. Ed. Engl. 8, 54 (1969)
Nesmeyanov, A. N., Tolstaya, T. P., Grib, A. V.: Dokl. Akad. Nauk SSSR, 153, 608 (1963), (C. A. 60, 6812b (1964))
Nesmeyanov, A. N. et al.: Dokl. Akad. Nauk SSSR 199, 610 (1971), (C. A. 75, 140 574p (1971))
Nesmeyanov, A. N. et al.: Izvest. Akad. Nauk SSSR, Ser. Khim. 1973, 2632, (C. A. 81, 49 503c (1974))
Hellwinkel, D., Seifert, H.: Chem. Ber. 105, 880 (1972)
Hellwinkel, D., Seifert, H.: Liebigs Ann. Chem. 762, 29 (1972)
See Wittig, G., Benz, E.: Chem. Ber. 92, 1999 (1959)
Hoffmann, R. W.: Dehydrobenzene and Cycloalkynes, Verlag Chemie, Winheim/Bergstraße 1967, p. 173
Seyferth, D., Hughes, W. B., Heeren, J. K.: J. Amer. Chem. Soc. 87, 2847, 3467 (1965)
Katz, T. J., Turnblom, E. W.: J. Amer. Chem. Soc. 92, 6701 (1970)
Turnblom, E. W., Katz, T. J.: ibid. 93, 4065 (1971)
Turnblom, E. W., Katz, T. J.: J. C. S. Chem. Commun. 1972, 1270
Turnblom, E. W., Katz, T. J.: J. Amer. Chem. Soc. 95, 4292 (1973)
Bushweller, C. H. et al.: Tetrahedron Letters 1972, 2401
Cremer, S. E. et al.: J. C. S. Chem. Commun. 1975, 374
Turnblom, E. W., Hellwinkel, D.: ibid. 1972, 404
For a recent review see Schmidbaur, H.: Adv. Organomet. Chem. 14, 205 (1976)
Schmidbaur, H., Wolf, W.: Chem. Ber. 108, 2834, 2842, 2851 (1975)
Schmidbaur, H., Holl, P., Köhler, F. H.: Angew. Chem. 89, 748 (1977); Angew. Chem. Internat. Ed. Engl. 16, 722 (1977)
Schmidbaur, H., Holl, P.: Z. Anorg. Allg. Chem. 458, 249 (1979)
The, K. I., Cavell, R. G.: J. C. S. Chem. Commun. 1975, 716
Cavell, R. G., Gibson, J. A., The, K. I.: J. Amer. Chem. Soc. 99, 7841 (1977)
Cavell, R. G., Gibson, J. A., The, K. I.: Inorg. Chem. 17, 2880 (1978)
Douglas, J. E.: Inorg. Chem. 11, 654 (1972)
See also Reddy, G. S., Weis, C. D.: J. Org. Chem. 28, 1822 (1963)
Denney, D. B., Denney, D. Z., Hsu, Y. F.: Phosphorus 4, 217 (1974)
See for example Hellwinkel, D. in: Organic Phosphorus Compounds, Vol. 3, (ed. Kosolapoff, G. M., Maier, L.) Wiley, New York 1972, p 185
Wittig, G., Hellwinkel, D.: Chem. Ber. 97, 769 (1964)
Hellwinkel, D., Kilthau, G.: ibid. 101, 121 (1968)
Hellwinkel, D., Knabe, B.: ibid. 104, 1761 (1971)
Hellwinkel, D., Kilthau, G.: Angew. Chem. 78, 1018 (1966), Angew. Chem. Internat. Ed. Engl. 5, 969 (1966)
Ross, B. W., Marzi, W. B.: Chem. Ber. 108, 1518 (1975)
Beattie, I. R. et al.: J. C. S. Dalton Transactions 1972, 784
See also McKay, K. M., Sowerby, D. B., Young, W. C.: Spectrochim. Acta A24, 611 (1968)
Brock, C. P., Webster, D. F.: Acta Crystall. B 32, 2089 (1976)
Hellwinkel, D., Knabe, B.: Phosphorus 2, 129 (1972)
Hellwinkel, D., Knabe, B., Kilthau, G.: J. Organometal. Chem. 24, 165 (1970)
Grim, S. O., Seyferth, D.: Chem. Ind. 1959, 849
Wittig, G., Henry, M. C.: J. Amer. Chem. Soc. 82, 563 (1960)
Seyferth, D., Cohen, H. M.: J. Inorg. Nucl. Chem. 20, 73 (1961)
Mitschke, K. H., Schmidbaur, H.: Chem. Ber. 106, 3645 (1973)
Ott, R., Weidlein, J., Mitschke, K. H.: Chimia 29, 262 (1975)
Eberwein, B., Ott, R., Weidlein, J.: Z. Anorg. Allg. Chem. 431, 95 (1977)
Wittig, G., Hellwinkel, D.: Chem. Ber. 97, 789 (1964)
Hellwinkel, D., Bach, M.: J. Organometal. Chem. 17, 389 (1969)
Doleshall, G., Nesmeyanov, N. A., Reutov, O. A.: ibid. 30, 369 (1971)
Hellwinkel, D., Bach, M.: ibid. 28, 349 (1971)
Hellwinkel, D., Bach, M.: ibid. 20, 273 (1969)
Sauers, R. R.: Chem. Ind. 1960, 717
Shen, K. W., McEwen, W. E., Wolf, A. P.: J. Amer. Chem. Soc. 91, 1283 (1969)
Nefedov, V. D., Kirin, I. S., Zaitsev, V. M.: Radiokhimiya 6, 78 (1964), (C. A. 61, 3876g, 3877d (1964))
Razuvaev, G. A. et al.: Zhur. Obshch. Khim. 30, 3234 (1960), (C. A. 55, 21010c (1961))
Razuvaev, G. A., Osanova, N. A., Sangalov, Y. A.: Zhur. Obshch. Khim. 37, 216 (1967), (C. A. 66, 95 139b (1967))
McEwen, W. E., Lin, C. T.: Phosphorus 4, 91 (1974)
Raynier, B. et al.: Nouv. J. Chem. 3, 393 (1979)
Angelelli, J. M. et al.: J. Amer. Chem. Soc. 91, 4500 (1969)
See also Taft, R. W. et al. ibid. 85, 3146 (1963)
Nesmeyanov, A. N., Mikul'shina, V. V., Reutov, O. A.: Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 2397), (C. A. 86, 72788m (1977)); Dokl. Akad. Nauk SSSR 237, 1111 (1977), (C. A. 88, 120 704w (1978))
Sowerby, D. B.: J. Chem. Res. (S) 1979, 80
Briles, G. H., McEwen, W. E.: Tetrahedron Letters 1966, 5191
Chupka Jr., F. L., Knapczyk, J. W., McEwen, W. E.: J. Org. Chem. 42, 1399 (1977)
Lanneau, G. F. et al.: J. Organometal. Chem. 85, 179 (1975)
McEwen, W. E., Lin, C. T.: Phosphorus 3, 229 (1974)
Matsuda, H., Ninagawa, A., Nomura, R.: Chem. Letters 1979, 1261
Wheatly, P. J.: J. Chem. Soc. 1964, 3718
Beauchamp, A. L., Bennett, M. J., Cotton, F. A.: J. Amer. Chem. Soc. 90, 6675 (1968)
Such solvates had already been identified by Wittig and Clauß 25)
Brabant, C., Blanck, B., Beauchamp, A. L.: J. Organometal. Chem. 82, 231 (1974)
Brabant, C., Hubert, J., Beauchamp, A. L.: Canad. J. Chem. 51, 2952 (1973)
Kuykendall, G. L., Mills, J. L.: J. Organometal. Chem. 118, 123 (1976)
Brock, C. P.: Acta Crystall. A 33, 193, 898 (1977)
Brock, C. P., Ibers, J. A.: ibid. A32, 38 (1976)
Weiss, J.: Heidelberg, 1964, unpublished
Hellwinkel, D., Bach, M.: Naturwissenschaften 54, 214 (1969)
Takashi, Y.: J. Organometal. Chem. 8, 225 (1967)
Cowley, A. H. et al.: J. Amer. Chem. Soc. 93, 2150 (1971)
Nesmeyanov, A. N., Borisov, A. E., Kizim, N. G.: Izv. Acad. Nauk SSSR, Ser. Khim. 1974, 1672 (C. A. 81, 105652q (1974))
Meinema, H. A., Noltes, J. G.: J. Organometal. Chem. 22, 653 (1970)
Tempel, N., Schwarz, W., Weidlein, J.: ibid. 154, 21 (1978)
Schmidbaur, H., Haßlberger, G.: Chem. Ber. 111, 2702 (1978)
Downs, A. J., Schmutzler, R., Steer, I. A.: J. C. S. Chem. Commun. 1966, 221
Holmes, R. R., Deiters, R. M., Golen, J. A.: Inorg. Chem. 8, 2612 (1969)
Muetterties, E. L. et al.: ibid. 3, 1298 (1964)
For a review see Schmidbaur, H.: Adv. Organomet. Chem. 14, 232 (1976)
Schmidbaur, H., Weidlein, J., Mitschke, K. H.: Chem. Ber. 102, 4136 (1969)
Schmidbaur, H., Mitschke, K. H.: ibid. 104, 1837, 1842 (1971)
Schmidbaur, H., Mitschke, K. H., Weidlein, J.: Z. Anorg. Allg. Chem. 386, 147 (1971)
Graves, G. E., Van Wazer, J. R.: J. Organometal. Chem. 150, 233 (1978)
Eberwein, B., Weidlein, J.: Z. Anorg. Allg. Chem. 420, 229 (1976)
Bos, K. D. et al.: J. Organometal. Chem. 168, 159 (1979)
Schmidbaur, H., Mitschke, K. H.: Angew. Chem. 83, 149 (1971), Angew. Chem. Internat. Ed. Engl. 10, 136 (1971)
Nesmeyanov, A. N., Borisov, A. E., Novikova, N. V.: Izv. Akad. Nauk SSSR Otdel. Khim. Nauk 1960, 952, (C. A. 54, 24351a (1960))
Nesmeyanov, A. N., Borisov, A. E., Novikova, N. V.: ibid. 1960, 147; 1961, 612 (C. A. 54, 20 853d (1960), 55, 22 100c (1961)); Tetrahedron Letters 1960 (8), 23
Nesmeyanov, A. N., Borisov, A. E., Novikova, N. V.: Izv. Akad. Nauk SSSR Otdel. Khim. Nauk 1961, 1578; 1964, 1202 (C. A. 56, 4792d (1962); 61, 12032f (1964))
Nesmeyanov, A. N., Borisov, A. E., Novikova, N. V.: ibid. 1961, 730; 1964, 1197 (C. A. 55, 22 101e (1961); 61, 12032a (1964))
Hellwinkel, D., Bach, M.: Liebigs Ann. Chem. 720, 198 (1968)
Razuvaev, G. A., Osanova, N. A., Sharutin, V. V.: Dokl. Akad. Nauk SSSR 225, 581 (1975) (C. A. 84, 105 704v (1976))
Razuvaev, G. A. et al.: ibid. 238, 361 (1978) (C. A. 88, 105 499q (1978))
Barton, D. H. et al.: J. C. S. Chem. Commun. 1980, 827
Nefedov, V. D. et al.: Radiokhimiya 6, 632 (1964) (C. A. 62, 3600d (1965))
Goel, R. G., Prasad, H. S.: J. Organometal. Chem. 50, 129 (1973)
Tel'noi, V. I., Rabinovich, I. B.: Usp. Khim. 49, 1137 (1980)
Clauß, K.: Chem. Ber. 88, 268 (1955). See also Hellwinkel, D., Haltmeier, M., Reiff, G.: Liebigs Ann. Chem. 1975, 249
Wittig, G., Fritz, H.: ibid. 577, 39 (1952)
Hellwinkel, D., Fahrbach, G.: ibid. 712, 1 (1968); 715, 68 (1968); Chem. Ber. 101, 574 (1968)
Hellwinkel, D.: Annals of the New York Academy of Sciences 192, 158 (1972)
For some key references see Kutzelnigg, W., Wallmeier, H., Wasilewski, J.: Theor. Chim. Acta 51, 261 (1979)
Strich, A., Veillard, A.: J. Amer. Chem. Soc. 95, 5574 (1973)
Florey, J. B., Cusachs, L. C.: ibid. 94, 3040 (1972)
Rauk, A., Allen, L. C., Mislow, K.: ibid. 94, 3035 (1972)
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Hellwinkel, D. (1983). Penta- and hexaorganyl derivatives of the main group five elements. In: Wittig Chemistry. Topics in Current Chemistry, vol 109. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0018055
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