Abstract
The research of recent years on the synthesis of new types of phosphoranes with P-O bonds (oxaphosphoranes) is examined. Particular attention is directed to the problems of the thermodynamic stabilities of oxaphosphoranes and the homolytic reactions of hydrooxaphosphoranes.
Similar content being viewed by others
Literature Cited
N. A. Polezhaeva and R. A. Cherkasov, Usp. Khim., 54, 1899 (1985).
H. Y. Khorana, Y. M. Tener, R. S. Wright, and J. Y. Morffatt, J. Am. Chem. Soc., 79, 430 (1957).
V. Dakess, D. F. W. Gross, and T. Taylor, British Patent No. 1180398; Chem. Abstr., 72, 101644 (1970).
M. Yoshizawa, T. Mikami, M. Kobayashi, and A. Yido, US Patent No. 3760037; Chem. Abstr. 80, 71534 (1974).
Ch. Lassanniere and E. L. Pierre, West German Patent No. 2359245; Chem. Abstr., 81, 204 (1974).
P. Borrewang, E. Yuddal, H. B. Peterson, P. Farrup, and J. I. Nielsen, West German Patent No. 2364749; Chem. Abstr., 81, 105547 (1974).
S. Seki and T. Yashiaru, West German Patent No. 24180898; Chem. Abstr., 82, 57711 (1975).
S. Stournas, R. F. Bridger, and E. A. Hella, US Patent No. 3795612; Chem. Abstr., 81, 15559 (1974).
F. Komaz and F. Erben, Czechoslovakian Patent No. 157898; Chem. Abstr, 83, 194595 (1975).
T. Mitsuda, S. Kobayashi, and P. Hasimoto, Japanese Patent No. 7927566; Chem. Abstr., 90, 203681 (1979).
F. H. Osman, Y. M. M. Abdel, and M. Ablashi, J. Chem. Soc., Perkin I, No. 6, 1189 (1984).
M. A. Pudovik, S. A. Terent'eva, and A. N. Pudovik, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1408 (1982).
Y. H. L. Cragg, B. Dawidowitch, Y. U. Fazakerley, L. R. Nasssimbebin, and R. J. Hains, Chem. Commun., No. 12, 510 (1978).
R. S. Mukhametov and E. E. Korshin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 493 (1985).
W. J. Richter, Phosph. Sulfur, 10, 395 (1981).
I. F. Lutsenko and M. V. Proskurnina, Usp. Khim., 47, 1648 (1978).
M. A. Pudovik, Yu. B. Mikhailov, and T. A. Malykh, Zh. Obshch. Khim., 50, 1677 (1980).
A. A. Prishchenko, A. V. Gromov, and I. F. Lutsenko, Zh. Obshch. Khim., 54, 712 (1984).
M. Sanchez, J. F. Bazier, D. Houallo, and K. Wolf, Bull. Soc. Chim. France, No. 10, 3930 (1967).
M. A. Pudovik, Yu. B. Mikhailov, and A. N. Pudovik, Zh. Obshch. Khim., 55, 1184 (1985).
Chang Cong, A. Munoz, M. Koenig, and K. Wolf, Tetrahedron Lett., No. 26, 2297 (1977).
M. T. Boisdon, B. Malavand, and J. Barrans, Phosph. Sulfur, 8, 305 (1980).
R. Burgada, Y. El. Leroux, and Y. O. Khoshinich, Tetrahedron Lett., No. 10, 925 (1980).
S. A. Terent'eva, M. A. Pudovik, and A. N. Pudovik, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1897 (1976).
M. A. Pudovik, V. V. Ovchinnikov, R. A. Cherkasov, and A. N. Pudovik, Usp. Khim., 52, 646 (1983).
M. T. Boisdon, C. Malavand, F. Mathis, and S. Barans, Tetrahedron Lett., No. 39, 3501 (1977).
M. A. Pudovik, S. A. Terent'eva, and A. N. Pudovik, Dokl. Akad. Nauk SSSR, 228, 363 (1976).
M. A. Pudovik, S. A. Terent'eva, Yu. B. Mikhailov, and A. N. Pudovik, Zh. Obshch. Khim., 52, 1302 (1982).
R. Fuks, M. Strebelle, and A. Wenders, Synthesis, No. 4, 788 (1977).
M. A. Pudovik, S. A. Terent'eva, and A. N. Pudovik, Zh. Obshch. Khim., 52, 491 (1982).
I. F. Lutsenko, M. V. Proskurnina, and A. A. Borisenko, Dokl. Akad. Nauk SSSR, 194, 828 (1970).
D. Houalla, H. Ramdone, and R. Wolf, New J. Chem., 9, 198 (1985).
F. Ramirez, Bull. Soc. Chim. France, No. 10, 3419 (1970).
D. B. Denney, D. Z. Denney, P. Y. Hommond, and Yu.-Piu Wang, J. Am. Chem. Soc., 103, 1785 (1981).
D. B. Denney and D. H. Jones, J. Am. Chem. Soc., 91, 5821 (1969).
E. Kraweczyk, J. Micholski, and A. Skowronska, Tetrahedron Lett., No. 23, 2019 (1977).
Zin dun-Zu and Liu-Li-Huansye, Acta Chim., 43, 298 (1985).
D. B. Denney, D. Z. Denney, and Li-Tsu Liu, Phosph. Sulfur, 3, 243 (1982).
V. P. Kukhar', E. V. Grishkun, V. P. Rudavskii, and V. A. Gilyarov, Zh. Obshch. Khim., 50, 1477 (1980).
D. B. Denney, D. Z. Denney, and J. J. Gigantino, J. Org. Chem., 49, 2831 (1984).
L. N. Markovskii, N. P. Kolesnik, and Yu. G. Shermolovich, Zh. Obshch. Khim., 50, 826 (1980).
D. D. Denney, Z. D. Denney, P. J. Hammond, C. Huang, Dun-Tsu-Diu, and Kuo-Shi-Tseng, Phosph. Sulfur, 15, 281 (1983).
L. Citerio, L. Pocar, and R. Stradi, J. Chem. Soc., Perkin I, No. 3, 309 (1978).
B. J. Swanson, J. C. Crockett, and T. H. Koch, J. Org. Chem., 46, 1082 (1981).
V. V. Ovchinnikov, Yu. G. Evstaf'eva, R. A. Cherkasov, and A. N. Pudovik, Zh. Obshch. Khim., 53, 1923 (1983).
D. B. Denney, D. Z. Denney, D. M. Gabrilovic, et al., J. Am. Chem. Soc., 102, 7072 (1980).
A. Schnidpeter and J. H. Weinnoier, Angew. Chem., 87, 517 (1975).
S. D. Harper and A. Arduengo, J. Am. Chem. Soc., 104, 2497 (1982).
J. Hoinicke and A. Fzschoch, Tetrahedron Lett., No. 49, 5481 (1983).
A. Mustofa, M. M. Sidky, and F. F. Soliman, Tetrahedron, 22, 393 (1966).
Kh. I. Riisalu, V. V. Vasil'ev, and B. I. Ionin, Zh. Obshch. Khim., 54, 563 (1984).
W. Stonser, Y. V. Röschenthaler, R. Schutzler, and W. S. Cheldrick, Chem. Ber., 114, 3609 (1981).
R. Francke, R. Di, Jiacomo, D. Daktermieks, and Y. V. Roschenthaler, Z. Anorg. Allg. Chem., 519. No. 12, 141 (1984).
I. V. Konovalova, L. A. Burnaeva, N. M. Konstantinova, and A. N. Pudovik, Zh. Obshch. Khim., 52, 1965 (1982).
M. Benhammon, R. Kraemer, H. Germa, J. P. Majoral, and J. Narech, Phosph. Sulfur, 14, 105 (1981); Ref. Zh. Khim., 19Zh351 (1983).
H. Fauduet and R. Burgada, Compt. Rend., C, 291, 81 (1980).
M. M. Sidky, M. F. Zayed, A. A. El-Katel, and P. Hennway, Phosph. Sulfur, 9, 343 (1981).
K. C. Caster and L. D. Quin, Tetrahedron Lett., No. 52, 5831 (1983).
M. Instein and J. D. Jenkins, Chem. Commun., No. 2, 164 (1983).
T. N. Kudryavtseva, M. V. Proskurnina, and I. F. Lutsenko, Zh. Obshch. Khim., 51, 1664 (1981).
J. Navech, Tetrahedron Lett., No. 25, 2863 (1986).
J. Leroux, D. El. Manoui, and R. Burgada, Tetrahedron Lett., No. 35, 3393 (1981).
J. Kimura, M. Migamoto, and T. Saedusa, J. Org. Chem., 47, 916 (1982).
J. C. Caesar, D. Griffits, J. C. Febby, and S. E. Eilletts, J. Chem. Soc., Dalton, No. 7, 1627 (1984).
M. R. Mahran and W. M. Abdo, Egypt. J. Chem., 21, 469 (1978); Ref. Zh. Khim., 14Zh311 (1981).
J. Gloede, H. Gross, J. Miehalski, M. Pakulsko, and A. Shourouska, Phosph. Sulfur, 13, 157 (1983).
H. Meggendorter, R. Schwarts, and I. Ugi, Tetrahedron Lett., No. 26, 2493 (1980).
M. N. Danchenko and A. D. Sinitsa, Zh. Obshch. Khim., 54, 473 (1984).
J. Burski, J. Kieszkowski, J. Michalski, H. Pakulski, and A. Skowrowska, Tetrahedron Lett., No. 24, 4175 (1983).
J. Gloede, Z. Chem., 26, 247 (1986).
W. Storzer, D. Schomburg, and G. V. Röschenthaler, Z. Naturforsch., 36, 1091 (1981).
K. Tanaka, T. Ygarashi, and K. Mitsuhashi, Heterocycles, 20, 157 (1983).
A. Baceinedo, G. Bertrand, J. P. Majoral, U. Wermuth, and R. Schmitzlen, J. Am. Chem. Soc., 106, 7065 (L984).
S. K. Tupchienko, T. N. Dudchenko, and A. D. Sinitsa, Zh. Obshch. Khim., 55, 11 (1985).
H. W. Rolsky and H. Djarroh, Inorg. Chem., 21, 844 (1982).
G. V. Roschenthaler and W. Storzer, Angew. Chem., 94, 212 (1982).
G. V. Roschenthaler, E. Bohlen, W. Störzer, A. E. Sopchik, and W. G. Bentrude, Z. Anorg. Allg. Chem., 507, No. 12, 93 (1983).
L. Lamande, A. Muenoz, and D. Boyer, Chem. Commun., No. 4, 225 (1984).
J. Granoth and J. C. Martin, J. Am. Chem. Soc., 101, 4618 (1979).
J. Sigall and I. Granoth, J. Am. Chem. Soc., 101, 3687 (1979).
A. Munoz, M. Galligher, A. Klaebe, and R. Wolf, Tetrahedron Lett., No. 9, 673 (1976).
J. Cadogan, I. Gosney, E. Henry, T. Naisby, B. Nay, N. J. Steevart, and N. J. Tweddle, Chem. Commun., No. 4, 189 (L979).
A. Willeit, E. P. Muller, and B. Reringer, Helv. Chim. Acta, 66, 2467 (1983).
G. Baccolini, P. Spagnolo, and P. E. Todesco, Phosph. Sulfur, 8, 127 (1970).
V. P. Kukhar', E. V. Grishkun, and V. P. Rudavskii, Zh. Obshch. Khim., 50, 1017 (1980).
M. V. Proskurnina, T. N. Kudryavtseva, N. B. Karlstadt, T. G. Shestakova, and I. F. Lutsenko, Zh. Obshch. Khim., 50, 947 (1980).
T. N. Kudryavtseva, Master's Dissertation, Msocow State University, Moscow (1982).
T. N. Kudryavtseva, N. B. Karlstadt, T. G. Shestakova, M. V. Proskurnina, and I. F. Lutsenko, The Chemistry and Practical Application of Organosilicon and Organophosphorus Compounds [in Russian], Nauka, Leningrad (1980), p. 96.
H. W. Rocksy, K. Ambrosins, M. Bonek, and W. S. Sheldrick, Chem. Ber., 113, 1847 (1980).
F. Ugi and R. Schwars, Angew. Chem., 93, 836 (1981).
W. S. Sheldrick, N. Weferling, and R. Schmutzler, Annalen, No. 6, 1035 (1981).
I. Granoth, R. Alkoberts, and I. Sagall, Chem. Commun., No. 12, 622 (1981).
F. Ramirez, Acc. Chem. Res., 1, 168 (1968).
H. Gross and I. Gloede, Chem. Ber., 96, 1387 (1960).
B. A. Arbuzov and N. A. Polezhaeva, Usp. Khim., 43, 933 (1974).
V. V. Ragulin, A. A. Petrov, V. I. Zakharov, and N. A. Razumovich, Zh. Obshch. Khim., 52, 239 (1982).
R. O. Day, A. C. Sau, and R. R. Holmes, J. Am. Chem. Soc., 101, 3790 (1979).
A. F. Grapov, L. V. Rakhvodovskaya, and N. N. Mel'nikov, Usp. Khim., 50, 606 (1981).
L. N. Markovskii, A. V. Solov'ev, M. I. Povolotskii, and Yu. G. Shermolovich, Zh. Obshch. Khim., 53, 1549 (1983).
L. N. Markovskii, A. V. Solov'ev, V. V. Pirozhenko, and Yu. G. Shermolovich, Zh. Obshch. Khim., 51, 1950 (1981).
V. V. Ovchinnikov, Yu. G. Evstaf'eva, R. A. Cherkasov, and A. N. Pudovik, Zh. Obshch. Khim., 53, 1923 (1983).
I. V. Konovalova, N. V. Mikhailova, L. A. Burnaeva, and A. N. Pudovik, Zh. Obshch. Khim., 52, 1290 (1982).
H. J. Bestmann and K. Roth, Angew. Chem., 93, 584 (1981).
E. M. Rokhmin, Yu. B. Zeifman, Yu. A. Cheburkov, Yu. A. Gambaryan, and I. L. Knunyants., Dokl. Akad. Nauk SSSR, 161, 1356 (1965).
F. Ramirez, C. P. Smith, and J. F. Piloy, J. Am. Chem. Soc., 90, 6724 (1968).
M. A. Pudovik, G. V. Romanov, and R. L. Nazmutdinov, Zh. Obshch. Khim., 49; 257 (1979).
M. A. Pudovik, S. A. Terent'eva, Yu. Yu. Samitov, and A. N. Pudovik, Zh. Obshch. Khim., 45, 226 (1975).
M. A. Pudovik, A. N. Pudovik, S. A. Terent'eva, A. A. Karelov, and E. I. Gol'dfarb, Zh. Obshch. Khim., 50, 740 (1980).
H. Concoloves and I. Majoral, Phosph. Sulfur, 4, 357 (1978).
H. Concoloves and I. Majoral, Phosph. Sulfur, 4, 372 (1978).
D. B. Dennay and Li Shang Shin, J. Am. Chem. Soc., 96, 317 (1974).
R. Burgada, The Chemistry and Application of Organophosphorus Compounds [Russian translation], Nauka, Moscow (1974), p. 232.
Ph. Jarignac, B. Richard, Y. Leroux, and R. Burgada, J. Organomet. Chem., 93, 331 (1975).
I. Granoth and I. C. Martin, J. Am. Chem. Soc., 101, 4623 (1979).
J. Nielsen and O. Dahl, J. Chem. Soc., Perkin 2, No. 3, 553 (1984).
I. E. Richman, R. O. Day, and R. R. Holmes, Inorg. Chem., 20, 3378 (1981).
R. Khegen and G. R. J. Thatcher, J. Org. Chem., 51, 207 (1986).
I. Granoth and J. C. Martin, J. Am. Chem. Soc., 100, 5229 (1978).
S. Kobayashi, Y. Narukawa, T. Hashimoto, and T. Saegusa, Chem. Lett., No. 7, 1599 (1980).
N. S. Zefirov, N. V. Zyk, and M. V. Proskurnina, Sixth International Conference on Organic Synthesis: Program and Abstracts of Papers, D.032, Moscow (1986).
Ya. A. Levin and E. I. Vorkunova, The Homolytic Chemistry of Phosphorus [in Russian], Nauka, Moscow (1978), p. 270.
H. Kiefer and T. G. Traylor, Tetrahedron Lett., No. 49, 6163 (1966).
L. Z. Rol'nik, M. V. Proskurnina, T. N. Kudryavtseva, E. V. Pastushenko, S. S. Zlotskii, D. L. Rakhmankulov and I. F. Lutsenko, Zh. Obshch. Khim., 52, 1067 (1982).
F. M. Akhmetkhanova, L. Z. Rol'nik, M. V. Proskurnina, E. V. Pastushenko, S. S. Zlotskii, and D. L. Rakhmankulov, Zh. Obshch. Khim., 55, 2039 (1985).
F. M. Akhmetkhanova, L. Z. Rol'nik, M. V. Proskurnina, E. V. Pastushenko, S. S. Zlotskii, and D. L. Rakhmankulov, Zh. Obshch. Khim., 55, 2800 (1985).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1171, September, 1989.
Rights and permissions
About this article
Cite this article
Proskurnina, M.V., Zlotskii, S.S., Akhmetkhanova, F.M. et al. Chemistry of oxaphosphoranes (review). Chem Heterocycl Compd 25, 963–978 (1989). https://doi.org/10.1007/BF00487293
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00487293