Abstract
Toxicity of fluoroaromatic compounds is similar to that of the corresponding non-fluorinated hydrocarbons. Some polyfluoroaromatic compounds are considerably less toxic than their nonfluorinated analogues (e.g. hexafluorobenzene is just slightly toxic), whereas other compounds (e.g. octafluorotoluene and octafluoronaphthalene) are somewhat more toxic. Pentafluorobenzaldehyde is about ten times as toxic as benzaldehyde.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Organic Reactions, vol. 5. R. Adams (ed). Wiley, New York, 1949.
Organic Synthesis, Coll. Vol. 2. A. Blatt (ed). Wiley, New York, 1946.
USSR Pat. 279,608; C.A. 74, 64044 (1971). Brit. Pat. 1,130,263; C.A. 70, 47063 (1969)
Grakauskas, V.: J. Org. Chem. 34, 2835 (1964)
Shaw, M. J., Hyman, H. H., Filler, R.: J. Am. Chem. Soc. 92, 6498 (1970)
Schiemann, G.: J. Prakt. Chem. 140, 97 (1934)
Nad, M. M., Talalaeyeva, T. V., Kazennikova, G. V., Kocheshkov, K. K.: Izv. Akad. Nauk SSSR Otd. Khim. Nauk 1959, 65
Chambers, R., Heyes, J., Musgrave, W.: Tetrahedron 19, 891 (1963)
Desirant, Y.: Bull. Soc. Chim. Belg. 67, 676 (1958)
Godsell, J., Stacey, M., Tatlow, J.: Nature (Lond.) 178, 199 (1956)
Godsell, J., Stacey, M., Tatlow, J.: Tetrahedron 2, 193 (1958)
Yakobson, G. G., Platonov, V. E., Vorozhtsov, N. N.: Zh. Obshch. Khim. 35, 1158 (1965)
Parshall, G.: J. Org. Chem. 27, 4649 (1962)
Evans, F., Tiley, P.: J. Chem. Soc. (Lond.) C 1966, 134
Counsell, I., Green, I., Hales, I., Martin, I.: Trans. Farad. Soc. 61, 212 (1965)
Birchall, J., Haszeldine, R.: J. Chem. Soc. (Lond.) 1959, 13
McBee, E., Lindgrem, V., Ligett, V.: Ind. Eng. Chem. 39, 378 (1947)
Vorozhtsov, N. N., Platonov, V. E., Yakobson, G. G.: Izv. Akad. Nauk SSSR Otd. Khim. Nauk 1963, 1524
Fuller, G.: J. Chem. Soc. (Lond.) 1965, 6264
Gething, B., Patrick, C., Tatlow, J., Banks, R., Barbour, A., Tipping, A.: Nature (Lond.) 183, 586 (1959)
Brit. Pat. 917,412; C.A. 59, 3831 (1963)
US Pat. 3,004,077; C.A. 59, 2711 (1963)
Brit. Pat. 917,413; C.A. 59, 3852 (1963)
Coe, P., Patrick, C., Tatlow, J.: Tetrahedron 9, 240 (1960)
Brooke, G., Chambers, R., Heyes, J., Musgrave, W.: Proc. Chem. Soc. Lond. 1963, 94
Brooke, G., Chambers, R., Heyes, J., Musgrave, W.: J. Chem. Soc. (Lond.) 1964, 729
Mobbs, R., Musgrave, W.: Chem. Ind. (Lond.)1961, 1268
Belg. Pat. 617,337; C.A. 58, 13841 (1963)
Chambers, R., Heaton, C., Musgrave, W.: J. Chem. Soc. (Lond.) C 1968, 1933
Désirant, Y.: Bull. Sci. Acad. R. Belg. 41, 759 (1955)
Hellmann, L., Peters, E., Pummer, W., Wall, L.: J. Am. Chem. Soc. 79, 5654 (1957)
US Pat. 2,927,138; C.A. 54, 14187 (1960)
Wall, L., Fearn, J., Pummer, W., Lowry, R.: J. Res. NBS 65 A, 239 (1961)
US Pat. 3,033,905; C.A. 57, 11099 (1962)
Birchall, J., Haszeldine, R., Parkinson, A.: J. Chem. Soc. (Lond.) 1961, 2204
Banks, R., Birchall, J., Haszeldine, R., Sim, J., Sutcliffe, H.: Proc. Chem. Soc. Lond. 1962, 281
Christe, K., Pavlath, A.: Chem. Ber. 97, 2092 (1964)
Yakobson, G. G., Steingarts, V. D., Vorozhtsov, Jr, N. N.: Izv. Akad. Nauk, Ser. Khim. 1964, 1551
US Pat. 2,488,216; C.A. 44, 1628 (1950)
Wall, L., Pummer, W., Fearn, J., Antonucci, J.: J. Res. NBS 67 A, 481 (1963)
Sokolov, S. V., Tataurov, G. P., Yuminov, V. S., Udilov, G. P., Nirenburg, N. Ya.: Zh. Obshch. Khim. 36, 362 (1966)
Gething, B., Patrick, C., Stacey, M., Tatlow, J.: Nature (Lond.) 183, 588 (1959)
Gething, B., Patrick, C., Tatlow, J.: J. Chem. Soc. (Lond.) 1962, 186
Fr. Pat. 1,393,516; (1965); Chem. Abstr., 63, 6916 (1965)
Banks, R., Ginsberg, A., Haszeldine, R.: Proc. Chem. Soc. Lond. 1960, 211
Banks, R., Haszeldine, R., Datham, J., Young, I.: Chem. Ind. (Lond.) 1964, 835; J. Chem. Soc. (Lond.) 1965, 594
Burdon, J., Gilman, D., Patrick, C, Stacey, M., Tatlow, J.: Nature (Lond.) 186, 231 (1960)
Chambers, R., Hutchinson, J., Musgrave, W.: J. Chem. Soc. (Lond.) 1964, 3573; Proc. Chem. Soc. Lond. 1964, 83
Brit. Pat. 914,933; C.A. 59, 1600 (1963)
Birchall, J., Hazard, R., Haszeldine, R., Wakalski, P.: J. Chem. Soc. (Lond.) C 1967, 47
Brooke, G., Forbes, E., Richardson, R., Stacey, M., Tatlow, J.: J. Chem. Soc. (Lond.)1965, 2088
Pummer, W., Wall, L.: J. Res. NBS 63 A, 167 (1959)
Callander, D., Coe, P., Tatlow, J.: Tetrahedron 22, 419 (1966)
Belf, L., Buxton, M., Fuller, G.: J. Chem. Soc. (Lond.) 1965, 3372
Yakobson, G. G., Shteingarts, V. D., Miroshnikov, A. I., Vorozhtsov, Jr, N. N.: Dokl. Akad. Nauk SSSR 159, 1109 (1964)
US Pat. 3,046,313; C.A. 57, 15003 (1962)
Brooke, G., Musgrave, W.: J. Chem. Soc. (Lond.) 1965, 1864
Birchall, J., Haszeldine, R., Parkinson, A.: J. Chem. Soc. (Lond.) 1962, 4966
Fr. Pat. 1,360,917; C.A. 61, 13235 (1964)
Nield, E., Stephens, R., Tatlow, J.: J. Chem. Soc. (Lond.) 1959, 166
Shchegoleva, G. S., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Izv. Akad. Nauk SSSR Ser. Khim. 1967, 708
Comaggi, G., Campbell, S., Perry, D. Stephens, R., Tatlow, J.: Tetrahedron 22, 1755 (1965)
Platonov, V. E., Senchenko, T. V., Malyuta, N. G., Yakobson, G. G.: Izv. Akad. Nauk SSSR Ser. Khim. 1973, 2827
Platonov, V. E., Senchenko, T. V., Yakobson, G. G.: Zh. Org. Khim. 12, 816 (1976)
Brovko, V. V., Sokolenko, V. A., Yakobson, G. G.: Zh. Org. Khim. 10, 2385 (1974)
Platonov, V. E., Furin, G. G., Malyuta, N. G., Yakobson, G. G.: Zh. Org. Khim. 8, 430 (1972)
Malyuta, N. G., Platonov, V. E., Furin, G. G., Yakobson, G. G.: Tetrahedron 31, 1201 (1975)
Harrison, D., Stacey, M., Stephens, R., Tatlow, J.: Tetrahedron 19, 1893 (1963)
US Pat. 3,511,883; Off. Gaz. 874, 606 (1970)
Banks, R., Harrison, A., Haszeldine, R.: J. Chem. Soc. (Lond.) C 1966, 2102
Platonov, V. E., Ermolenko, N. V., Yakobson, G. G., Vorozhtsov, Yr, N. N.: Izv. Akad. Nauk SSSR Ser. Khim. 1968, 2752
Yakhlakova, O. M., Mazalov, S. F., Tataurov, G. P., Ivanova, E. P., Platonov, V. E.: USSR Pat. 341, 786; C.A. 78, 15360 (1973)
Kolenko, I. P., Lundin, B. N., Abezgauz, F. I., Marek, E. I., Strizhevsky, I. L.: Zh. Obshch. Khim. 37, 1686 (1967)
Vorozhtsov, Yr, N. N., Yezersky, S. N., Kollegov, V. F. et al.: Izv. Akad. Nauk SSSR Ser. Khim. 1966, 1291
Vorozhtsov, Yr, N. N., Yermolenko, N. V., Mazalov, S. A., Osina, O. I., Platonov, V. E., Tyurin, V. S., Yakobson, G. G.: Izv. Akad. Nauk SSSR Ser. Khim. 1969, 196
Antonucci, J., Wall, L.: J. Res. NBS 70 A, 473 (1966)
Letchford, B., Patrick, C., Tatlow, J.: Tetrahedron 20, 1381 (1964)
Florin, R., Pummer, W., Wall, L.: J. Res. NBS 1959, 107
US Pat. 2,586,364; C.A. 8675 (1952)
Lock, G.: Chem. Ber. 69, 2553 (1936)
Pozdnyakovich, Yu. V., Shteingarts, V. D.: J. Fluor. Chem., 4, 317 (1974)
Fokin, E. P., Gerasimova, T. N., Vasilyevskaya, T. N., Baturina, I.I., Matoshina, K. I.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk. 1971, vyp. 4, N 9, 135
Platonov, V. E., Gatilova, V. P., Dvornikova, K. V., Yakobson, G. G.: Izv. Akad. Nauk SSSR Ser. Khim. 1974, 1668
Mobbs, R.: J. Fluor. Chem. 1, 361 (1972)
USSR Pat. 290,899; C.A. 74, 125121 (1971)
US Pat. 3,000,976; C.A. 57, 9736 (1962)
Brit. Pat. 917,413; C.A. 59, 3852 (1963)
Patrick, C. R., Pedler, A. E., Seabra, A., Stephens, R., Tatlow, J.: Chem. Ind. (Lond.)1963, 1557
USSR Pat. 370,195; C.A. 79, 18337 (1973)
USSR Pat. 255,230; C.A. 75, 88290 (1971)
USSR Pat. 405,891; C.A. 80, 146038 (1974)
Chambers, R., Corbally, R., Holmes, T., Musgrave, W.: J. Chem. Soc. (Lond.) Perkin Trans. 1, 1974, 108
Delyagina, N. I., Pervova, E. Ya., Dyatkin, B. L., Knunyants, I. L.: Zh. Org. Khim. 8, 851 (1972)
Yakobson, G. G., Shteingarts, V. D., Mironova, N. E., Vorozhtsov, Yt, N. N.: Zh. Obshch. Khim. 36, 145 (1966)
Burdon, J., Hollyhead, W., Tatlow, J.: J. Chem. Soc. (Lond.) 1965, 6336
Stephens, R., Tatlow, J.: Chem. Ind. (Lond.) 1957, 821
Johncock, P., Mobbs, R., Musgrave, W.: Ind. Eng. Chem. Proc. Des. Dev. 1, 267 (1962)
Coe, P., Croll, B., Patrick, C.: Tetrahedron 29, 2097 (1964)
Florin, R., Pummer, W., Wall, L.: J. Res. NBS 62, 119 (1959)
Tilney-Bassett, I.: Chem. Ind. (Lond.) 1965, 693
Vorozhtsov, Yr, N. N., Barkhash, B. A., Ivanova, N. G., Anichkina, S. A., Andreevskay, O. I.: Dokl. Akad. Nauk SSSR 759, 125 (1964)
Coe, P., Stephens, R., Tatlow, J.: J. Chem. Soc. (Lond.) 1962, 3227
Barbour, A., Buxton, M., Coe, P., Stephens, R., Tatlow, J.: J. Chem. Soc. (Lond.) 1961, 808
Coe, P., Plevey, R., Tatlow, J.: J. Chem. Soc. (Lond.) C 1969, 597
Vorozhtsov, Yr, N. N., Barkhash, V. A., Gerasimova, T. N., Lokshina, E.G.: Izv. Akad. Nauk SSSR Ser. Khim. 1965, 2086
Yakobson, G. G., Moronova, N. E., Petrov, A. K., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 36, 147 (1966)
Vorozhtsov, Yr, N. N., Barkhash, V. A., Gerasimova, T. N., Lokshina, E. G., Ivanova, N. G.: Zh. Obshch. Khim. 37, 1293 (1967)
Cohen, S., Reddy, M., Massey, A.: J. Chem. Soc. Chem. Commun. 1967, 451; J. Organometal. Chem. 11, 563 (1968)
Pummer, W., Wall, L.: J. Res. NBS 63 A, 167 (1959)
Bardin, V. V., Furin, G. G., Yakobson, G. G.: Zh. Org. Khim. 17, 999 (1981)
Birchall, J., Clarke, T., Haszeldine, R.: J. Chem. Soc. (Lond.) 1962, 4911
Ambrose, D.; J. Chem. Soc. (Lond.) A 1968, 1381
Birchall, J., Haszeldine, R.: J. Chem. Soc. (Lond.) 1961, 3719
Filler, R., Ayyangar, N., Gustowski, W., Kang, H.: J. Org. Chem. 34, 534 (1969)
Pummer, W., Wall, L.: Science, (Wash DC) 127, 643 (1958)
Harper, R., Soloski, E., Tamborski, Ch.: J. Org. Chem. 29, 2385 (1964)
Sayers, D., Stephens, R., Tatlow, J.: J. Chem. Soc. (Lend.) 1964, 3035
USSR Pat. 386,896; C.A. 79, 126055 (1973)
Pasquale, R., Tamborski, C.: J. Org. Chem. 34, 1736 (1969)
Letchford, B., Patrick, C., Stacey, M., Tatlow, J.: Chem. Ind. (Lond.)1962, 1472
Tamborski, C., Soloski, E., Pasquale, R.: J. Organometal. Chem. 15, 494 (1968)
Soloski, E., Ward, W., Tamborski, C.: J. Fluor. Chem. 2, 361 (1972)
Stacey, M., Tatlow, J. in: Advances in Fluorine Chemistry, Vol. 1. Stacey, M., Tatlow, J., Sharpe, A. (eds). Butterworths, London 1960, p. 203
US Pat. 3,513,206; C.A. 73, 26956 (1970)
Fr. Pat. 1,544,617; C.A. 71, 112689 (1969)
US Pat. 3,265,746; C.A. 65, 13602 (1966)
Antonucci, J., Brown, D., Wall, L. Abstr. 156th Natl. Am. Chem. Soc. Meeting, Div. Fluorine Chem. New York, paper 20 (1968)
Pedler, A., Tatlow, J., Uff, A.: Tetrahedron 25, 1597 (1969)
Brovko, V. V., Sokolenko, V. A., Yakobson, G. G.: Zh. Org. Khim. 10, 300 (1974)
Dvornikova, K. V., Platonov, V. E., Yakobson, G. G.: Zh. Org. Khim. 11, 2383 (1975)
Waugh, E., Walton, D.; J. Organometal. Chem. 39, 275 (1972)
Bogoradovsky, E. T., Zavgorodnii, V. S., Mingaleva, K. S., Petrov, A. A.: Zh, Obshch. Khim. 44, 142 (1974)
Barrow, I., Pedler, A.: Tetrahedron 39, 1829 (1976)
Molosnova, V. P., Vysochin, V. I., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Izv. Akad. Nauk SSSR Ser. Khim. 1969, 146
Filler, R., Rao, Y.: J. Org. Chem. 39, 3421 (1974)
Birchall, J., Bowden, F., Haszeldine, R., Lever, A.: J. Chem. Soc. (Lond.) A 1967, 747
Filler, R., Heffern, E.: J. Org. Chem. 32, 3249 (1967)
Brooke, J.; J. Chem. Soc. Perkin Trans. 1, 1974, 233; Tetrahedron Lett. 1971, 2377
Callander, D., Coe, P., Tatlow, J., Terrell, R.: J. Chem. Soc. (Lond.) C 1971, 1542
Webb, A., Gilman, H.: J. Organometal. Chem. 20, 281 (1969)
Dvornikova, K. V. Ph. D. Dissertation, Novosibirsk, 1982
Brit. Pat. 985,610
Molosnova, V. P., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 39, 1114 (1969)
McBee, E., Rapkin, E.: J. Am. Chem. Soc. 73, 1366 (1951)
Brewer, I., Eckhard, I., Heaney, H., Marples, B.: J. Chem. Soc. (Lond.) C 1968, 664
Filler, R., Woods, S., Frendenthal, A.: J. Org. Chem. 38, 811 (1973)
Vlasov, V. M., Yakobson, G. G.: Zh. Obshch. Khim. 39, 2071 (1969)
Fuller, G., Warwick, D.: Chem. Ind. (Lond.) 1965, 651
Petrova, T. D., Savchenko, T. I., Ardyukova, T. F., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1970, vyp. 3, 119
Ger. Pat. 1,168,419; C.A. 61, 3027 (1964)
Chapman, N., Clarke, K., Pinder, R., Sawhney, S.: J. Chem. Soc. (Lond.) C 1967, 293
Vysochin, V. I., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 39, 1607 (1969)
Brit. Pat. 923,115; C.A. 59, 9902 (1963)
Barkhash, V. A., Andreevskaya, O. I., Vorozhtsov, Yr, N. N.: Dokl. Akad. Nauk SSSR 166, 1343 (1966)
Prudchenko, A. T., Shchegoleva, G. S., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 37, 2487 (1967)
Chambers, R., Spring, D.: J. Chem. Soc. (Lond.) C 1968, 2394
Vorozhtsov, Yr, N. N., Barkhash, V. A., Anichkina, S. A.: Zh. Org. Khim. 2, 1903 (1966)
Pozdnyakovich, Y. V., Shteigarts, V. D.: J. Fluor. Chem. 4, 317 (1974)
Anichkina, S. A., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Zh. Org. Khim. 38, 2493 (1968)
Prudchenko, A. T., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Izv. Akad. Nauk SSSR Ser. Khim. 1965, 1798; Vorozhtsov, Yr, N. N., Barkhash, V. A., Prudchenko, A. T., Shchegoleva, G. S.: Zh. Obsch. Khim. 35, 1501 (1965)
Filler, R., Rao, Y., Biezais, A., Miller, F., Beaucaire, V.: J. Org. Chem. 35, 930 (1970)
Furin, G. G., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1974, vyp. 1, 78
Coe, P., Whitingham, A.: J. Chem. Soc. Perkin Trans. 1, 1974, 917
Brit. Pat. 1,102,692; C.A. 68, 115904 (1968)
Brit. Pat. 1,102,693; C.A. 69, 43602 (1968)
Shteingarts, V. D., Budnik, A. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1967, vyp. 3, 124
Sah, P., Peoples, S.: Arzneim.-Forsch. 11, 27 (1961); C.A. 57, 16466 (1962)
Burdon, J., Damodaran, V., Tatlow, J.: J. Chem. Soc. (Lond.) 1964, 763
Burdon, J., Castander, J., Tatlow, J.: J. Chem. Soc. (Lond.) 1964, 5017
Shteingarts, V. D., Budnik, A. G., Yakobson, G. G., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 37, 1537 (1967)
Wallenfels, K., Draber, W.: Chem. Ber. 90, 2819 (1957)
Yakobson, G. G., Shteingarts, V. D., Vorozhtsov, Yr, N. N.: Zh. Vses. Khim. Obshch. Im D.I. Mendeleeva 1964, 701
Niel, E., Tatlow, J.: Tetrahedron 8, 38 (1960)
Yakobson, G. G., Odinokov, B. N., Vorozhtsov, Yr, N. N.: Tetrahedron Lett. 1965, 4473
Odinokov, V. N., Yakobson, G. G., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 37, 176 (1967)
Christe, K., Pavlath, A.: Chem. Ber. 96, 2537 (1963)
Harper, R., Tamborski, C.: Chem. Ind. (Lond.) 1962, 1824
Letchford, B., Patrick, C., Stacey, M., Tatlow, J.: Chem. Ind. (Lond.) 1962, Uli
Belg. Pat. 623,680; C.A. 60, 1657 (1964)
Belf, L., Buxton, M., Fuller, G.: J. Chem. Soc. (Lond.) 1965, 3372
Felstead, E., Feilding, H., Wakefield, B.: J. Chem. Soc. (Lond.) 1966, 708
Birchall, J., Haszeldine, R., Jone, M.: J. Chem. Soc. (Lond.) C 1971, 1343
US Pat. 3,150,163; C.A. 61, 16010 (1964)
US Pat. 3,046, 313; C.A. 57, 15003 (1962)
Belg. Pat. 630,479; C.A. 61, 3033 (1964)
US Pat. 3,429,935; C.A. 70, 97376 (1969)
Yakobson, G. G., Odinokov, V. N., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 36, 139 (1966)
Yakobson, G. G., Shteingarts, V. D., Vorozhtsov, Yr, N. N.: Zh. Vses. Khim. Obshch. Im D.I. Mendeleeva 1964, 702
Gething, B., Patrick, C., Tatlow, J.: J. Chem. Soc. (Lond.) 1961, 1574
Belg. Pat. 615,347; C.A. 58, 473 (1963)
Brit. Pat. 986,892; C.A. 62, 16142 (1965)
Sartori, P., Golloch, A.: Chem. Ber. 101, 2004 (1968)
Yakobson, G.G., Odinokov, V. N., Petrova, T. D., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 34, 2953 (1964)
Tamborski, C., Soloski, E.: J. Org. Chem. 31, 743 (1966)
Rupp, E.: Ber. 29, 1629 (1896); Rabjohn, N.: J. Chem. Soc. (Lond.) 1948, 3518
Ueda, K., Hashiguchi, T.: Bull. Chem. Soc. Jpn 40, 688 (1967)
Jap. Pat. 6,928,493; C.A. 72, 66669 (1970)
Hellmann, N., Bilbo, A.: J. Am. Chem. Soc. 75, 4590 (1953)
Prudchenko, A. T., Barkhash, V. A., Vorozhtsov, Yr. N. N.: Izv. Akad. Nauk SSSR Ser. Khim. 1965, 1798
Shchegoleva, G. S., Petrov, A. K., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Khim. Geterotsikl. Soedin. 1970, 278
Prudchenko, A. T., Vovdenko, L. P., Barkhash, V. A., Vorozhtsov, Yr, N. N.: Khim. Geterotsikl. Soedin, 1968, 961
Vlasov, V. M., Yakobson, G. G.: Izv. Akad. Nauk SSSR Ser. Khim. 1969, 893
Petrova, T. D., Kann, L. I., Barkhash, V. A., Yakobson, G. G.: Khim. Geterotsikl. Soedin. 1969, 778
Vorozhtsov, Yr. N. N., Barkhash, V. A., Prudchenko, A. T., Khomenko, T. I.: Zh. Obshch. Khim. 35, 1501 (1965); Dokl. Akad. Nauk SSSR 164, 1046 (1965)
USSR Pat. 270,718; C.A. 73, 98622 (1970)
Alsop, D., Burdon, J., Tatlow, J.: J. Chem. Soc. (Lond.) 1962, 1801
Tamborski, C., Soloski, E.: J. Org. Chem. 31, 746 (1966); US Pat. 3,459,794; C.A. 71, 80959 (1969)
Ryan, T., Berner, K.: Spectrochim. Acta Part a Mol Spectrosc 25, 1155 (1969)
Belf, L., Buxton, M., Tilney-Bassett, J.: Tetrahedron 23, 4719 (1967)
Gerasimova, T. N., Semikolenova, N. V., Orlova, N. A., Fomenko, T. V., Fokin, E. P.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1975, vyp. 6, 54
Petrov, V. P., Koptjug, V. A.: Reakt. Sposobnost Org. Soedin. 3, 135 (1966)
Brit. Pat. 901, 880 (1962); Chem. Abstr. 58, 1411 (1962)
Germ. Pat. 1,146,890; Chem. Abstr. 59, 11331 (1963)
Connet, J.; Chem. Ind. (Lond.)1965, 1695
Vlasov, V. M., Yakobson, G. G.: Zh. Obshch. Khim. 39, 2071 (1969)
Vlasov, V. M., Yakobson, G. G.: Zh. Obshch. Khim. 39, 785 (1969)
Brit. Pat. 977,961; C.A. 63, 8266 (1965)
Markovsky, L. N., Furin, G. G., Shermolovich, Yu. G., Tychkina, O. N., Yakobson, G. G.: Zh. Obshch. Khim. 49, 710 (1979)
Forbes, E., Richardson, R., Stacey, M., Tatlow, J.: J. Chem. Soc. (Lond.) 1959, 2019
Pummer, W., Wall, L.: J. Res. NBS 68 A, 277 (1964)
Antonucci, J., Wall, L.: J. Res. NBS 71 A, 33 (1967)
US Pat. 3,394,190; C.A. 69, 58939 (1968)
Brit. Pat. 1,110,232; C.A. 68, 114245 (1968)
Budnik, A. G.: Ph. D. Dissertation, Novosibirsk, 1969
Budnik, A. G., Rusakov, S. L., Khomenko, E. I., Yakobson, G. G.: Zh. Org. Khim. 14, 1281 (1978)
Yakobson, G. G., Petrova, T. D., Kann, L. I., Savchenko, T. I., Petrov, A. K., Vorozhtsov, Yr. N.N.: Dokl. Akad. Nauk SSSR 158, 926 (1964)
Denivelle, L., Chesneau, R.: C.R. Acad. Sci. 254, 1646 (1962)
Birchall, J., Haszeldine, R., Nikokavouras, J., Wilks, E.: J. Chem. Soc. (Lond.) C 1971, 562
Furin, G. G.: Ph. D. Dissertation, Novosibirsk, 1969
Tataurov, G. P., Sokolov, S. V.: Zh. Obshch. Khim. 36, 537 (1966)
Robson, P., Stacey, M., Stephens, M., Tatlow, J.: J. Chem. Soc. (Lond.) 1960, 4754
Belenky, G. G., German, L. S., Knunyants, I. L., Furin, G. G., Yakobson, G. G.: Zh. Org. Khim. 12, 1183 (1976)
Furin, G. G., Terentieva, T. V., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1972, vyp. 6, 78
Deacon, G., Parratt, J.: J. Organometal. Chem. 22, 287 (1970)
Burdon, J., Coe, P., Fulton, M.: J. Chem. Soc. (Lond.) 1965, 2094
Belf, L., Buxton, M., Woiton, D.: Chem. Ind. (Lond.) 1966, 238
Cohen, S., Reddy, M., Massey, A.: Chem. Commun. 1967, 451
Cohen, S., Reddy, M., Massey, A.: J. Organometal. Chem. 11, 563 (1968)
Yakobson, G. G., Furin, G. G., Terentieva, T. V.: Zh. Org. Khim. 10, 799 (1974)
Yakobson, G. G., Furin, G. G., Terentieva, T. V.: Izv. Akad. Nauk SSSR Ser. Khim. 1972, 2128
Furin, G. G., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1976, vyp. 6, 120
Furin, G. G., Terentieva, T. V., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1972, vyp. 6, 78
Furin, G. G., Shchegoleva, L. N., Yakobson, G. G.: Zh. Org. Khim. 11, 1290 (1975)
Peach, M., Spinney, H. Can. J. Chem. 49, 644 (1971)
Chambers, R., Cunningham, J., Pyke, D.: Tetrahedron 24, 2783 (1968)
Chambers, R., Cunningham, J.: Chem. Commun. 1966, 469
Sheppard, W.: J. Am. Chem. Soc. 93, 5597 (1971)
Sartori, P., Bauer, G.: J. Fluor. Chem. 12, 203 (1978)
Nield, E., Stephens, R., Tatlow, J.: J. Chem. Soc. (Lond.) 1959, 166
Robson, P., Smith, T. A., Stephens, R., Tatlow, J.: J. Chem. Soc. (Lond.) 1963, 3692
Sartori, P., Golloch, A.: Chem. Ber. 103, 3936 (1970)
Niel, R., Peach, M., Spinney, H.: Inorg. Nucl. Chem. Lett. 6, 509 (1970)
Furin, G. G., Krupoder, S. A., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1976, vyp. 5, 146
Sheppard, R., Foster, S.: J. Fluor. Chem. 2, 53 (1972/1973)
Furin, G. G., Andreevskaya, O. I., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk Ser. Khim. Nauk 1980, vyp. 2, 100
Clase, H., Poole, R.: 6th Int. Symp. Fluor. Chem., Durham, England, A 14 (1971)
Furin, G. G., Avramenko, A. A., Nikonorov, Yu. I., Yakobson, G. G.: Zh. Org. Khim. 17, 1505(1981)
Forbes, E., Richardson, R., Tatlow, J.: Chem. Ind. (Lond.)1958, 630
Brooke, G., Burdon, J., Stacey, M., Tatlow, J.: J. Chem. Soc. (Lond) 1960, 1768
Holland, D., Moore, G., Tamborski, C.: J. Org. Chem. 29, 1562 (1964)
Yakobson, G. G., Shteingarts, V. D., Furin, G. G., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 34, 3514 (1964)
Belf, L., Buxton, M., Wotton, D.: Chem. Ind. (Lond.) 1966, 238
Petrova, T. D., Mamaev, V. P., Yakobson, G. G.: Izv. Akad. Nauk SSSR Ser. Khim. 1969, 679
Coe, P., Jukes, A., Tatlow, J.: J. Chem. Soc. (Lond.) C 1966, 2323
Holland, D., Moore, C., Tamborski, C.: Chem. Ind. (Lond.) 1965, 1376
Holland, D., Moore, C., Tamborski, C.: J. Org. Chem. 29, 3042 (1964)
Jukes, A., Gilman, H.: J. Organometal. Chem. 17, 145 (1969)
Brooke, G., Burdon, J., Tatlow, J.: J. Chem. Soc. (Lond.) 1962, 3253
Burdon, J., Coe, P., Marsh, C.: Tetrahedron 22, 1183 (1966)
Kobrina, L. S., Furin, G. G., Yakobson, G. G.: Zh. Obshch. Khim. 38, 514 (1968)
Brooke, J., Burdon, J., Tatlow, J.: J. Chem. Soc. (Lond.) 1961, 802
Robson, P., Roylance, J., Stephens, R., Tatlow, J., Worthington, R.: J. Chem. Soc. Suppl. 1, 1964, 5748
Doyle, A., Pedler, A.: J. Chem. Soc. (Lond.) C 1972, 282
Brit. Pat. 1,232,285; C.A. 75, 44321 (1971)
Akhmetova, N. E.: Ph. D. Dissertation, Novosibirsk, 1978
Budnik, A. G., Kalinichenko, N. V., Shteingarts, V. D.: Zh. Org. Khim. 10, 1923 (1974)
Birchall, J., Haszeldine, R., Kemp, J.: J. Chem. Soc. (Lond.) C 1970, 449
USSR Pat. 225,210; C.A. 70, 19797 (1969)
USSR Pat. 242,907; C.A. 71, 80937 (1969)
Yakobson, G. G., Furin, G. G., Kobrina, L. S., Vorozhtsov, Yr, N. N.: Zh. Obshch. Khim. 37, 1289(1967)
Shermolovich, Yu. G., Polumbrik, O. M., Markovsky, L. N., Saenko, E. P., Furin, G.G., Yakobson, G. G.: Zh. Org. Khim. 13, 2589 (1977)
Banks, R., Noakes, T.: J. Chem. Soc. Perkin Trans. 1 1976, 143
Savchenko, T. I., Petrova, T. D., Platonov, V. E., Yakobson, G. G.: J. Fluor. Chem. 9, 505 (1977)
Savchenko, T. I., Petrova, T. D., Platonov, V. E., Yakobson, G. G.: Zh. Org. Khim. 15, 1018 (1979)
Savchenko, T. I., Petrova, T. D., Kolesnikova, I. V., Platonov, V. E.; Izv. Akad. Nauk SSSR Ser. Khim. 1980, 1213
Koppang, R.: J. Fluor. Chem. 16, 479 (1980)
Brooke, G., Burdon, J., Tatlow, J.: Chem. Ind. (Lond.) 1961, 832
Castellano, J., Green, J., Kaufman, J.: J. Org. Chem. 31, 821 (1966)
Burdon, J., Morton, C., Thomas, D.: J. Chem. Soc. (Lond.) 1965, 2621
Pront, C., Coda, A., Forder, R., Kammer, B.: Cryst. Struct. Commun. 3, 39 (1974)
Birchall, J., Clarke, T., Haszeldine; R.: J. Chem. Soc. (Lond.) 1962, 4977
Kashkin, A. V., Bakhmutov, Yu. L., Marchenko, N. N.: Zh. Vses. Khim. Obshch. Im D.I. Mendeleeva 15, 591 (1970)
Zibarev, A. V., Golding, I. R., Sladkov, A. M., Furin, G. G., Yakobson, G. G.: Izv. Akad. Nauk SSSR Ser. Khim. 1979, 2536
Andreevskaya, O. I., Furin, G. G., Yakobson, G. G.: Zh. Org. Khim. 13, 1684 (1977)
Glemser, O., Halasz, S., Biermann, U.: Inorg. Nucl. Chem. Lett. 4, 591 (1978)
Zibarev, A. V., Dolenko, G. N., Krupoder, S. A., Mazalov, L. N., Poleshchuk, O. Kh., Furin, G. G., Yakobson, G. G.: Zh. Org. Khim. 16, 390 (1980)
Banks, R., Prakash, A.: Tetrahedron Lett. 1973, 99
Banks, R., Prakash, A.: J. Chem. Soc. Perkin Trans. 1 1974, 1365
Brokke, M., Goodall, B., Sheppard, G., Stone, F.: J. Chem. Soc. Dalton Trans. 1975, 591
Hudson, A., Pedler, A., Tatlow, J.: Tetrahedron 26, 3791 (1970)
Korobeinicheva, I. K., Andreevskaya, O. I., Podgornaya, M. I., Furin, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1982, vyp. 5, 103
Birchall, J., Haszeldine, R., Kemp, J.: J. Chem. Soc. (Lond.) C 1970, 1519
Abramovich, R., Challand, S.: J. Chem. Soc. Chem. Commun. 1972, 1160
Abramovich, R., Challand, S., Yamada, Y.: J. Org. Chem. 40, 1541 (1975)
Abramovich, R., Challand, S., Scriven, E.: J. Am. Chem. Soc. 94, 1374 (1972)
Birchall, J., Daniewski, W., Haszeldine, R., Holfen, D.: J. Chem. Soc. (Lond.) 1965, 6702
Fild, M., Glemser, O., Christoph, G.: Angew. Chem. Int. Ed. Engl. 3, 801 (1964)
Janzen, A., Rodesiler, P., Willis, C.: J. Chem. Soc. Chem. Commun. 1966, 672
Respers, W., Tamborski, C.: J. Org. Chem. 77, 619 (1968)
Whittingham, A., Jarvie, A.: J. Organometal. Chem. 13, 125 (1968)
Brit. Pat. 1,101,972; C.A. 68, 69119 (1968)
Wall, L., Donadio, R., Pummer, W.: J. Am. Chem. Soc. 82, 4846 (1960)
Fild, M., Glemser, O., Christoph, G.: Angew. Chem. Int. Ed. Engl. 23, 953 (1964)
Kemmitt, R., Nichols, D., Peacock, R.: Chem. Commun. 1967, 599
Emeleus, H., Miller, J.: J. Inorg. Nucl. Chem. 28, 662 (1966)
Andreevskaya, O. I., Krupoder, S. A., Furin, G. G., Yakobson, G. G.: Izv. Sib. Otd. Akad. Nauk SSSR Ser. Khim. Nauk 1980, vyp. 6, 97
Fild, M., Schmutzler, R.: J. Chem. Soc. (Lond.) A 1969, 840
Yakobson, G. G., Furin, G. G., Terentieva, T. V.: Zh. Org. Khim. 9, 1707 (1973)
Gibson, J., Janzen, A.: 6th Int. Symp. Fluor. Chem, Durham, England, C 26 (1971)
Furin, G. G., Terentieva, T. V., Rezvukhin, A. I., Yakobson, G. G.: Zh. Obshch. Khim. 45, 1473 (1975)
Markovsky, L. N., Furin, G. G., Shermolovich, Yu. G., Yakobson, G. G.: Izv. Akad. Nauk SSSR Ser. Khim. 1981, 867
US Pat. 3,341,631; C.A. 68, 29321 (1968)
Chambers, R., Coates, G., Livingstone, J., Musgrave, W.: J. Chem. Soc. (Lond.) 1962, 4367
Furin, G. G., Andreevskaya, O. I., Yakobson, G. G.: Zh. Org. Khim. 72, 2627 (1976)
Cohen, S., Massey, A.: J. Organometal. Chem. 10, 411 (1967)
Connett, J., Davies, A., Deacon, G., Green, J.: Chem. Ind. (Lond.) 1965, 512; J. Chem. Soc. (Lond.) 1966, 106
Maletina, I. I., Orda, V. V., Aleinikov, N. N., Korsunsky, B. L., Yagupolsky, L. M.: Zh. Org. Khim. 72, 1371 (1976)
Berny, J., Oates, G., Winfield, J.: J. Chem. Soc. Dalton Trans. 1974, 509
Lyalin, V. V., Orda, V. V., Alekseeva, L. A., Yagupolsky, L. M.: Zh. Org. Khim. 6, 329 (1970)
Brewer, I., Heaney, H.: Tetrahedron Lett., 1965, 4709
Vorozgtsov, Yr, N. N., Ivanova, N. G., Barkhash, V. A.: Zh. Org. Khim. 3, 220 (1967); Izv. Akad. Nauk SSSR Ser. Khim. 1967, 1514
Cohen, S., Fenton, D., Tomlunson, A., Massey, A.: J. Organometal. Chem. 6, 301 (1966)
Callander, D., Coe, P., Tatlow, J.: Tetrahedron 25, 25 (1969)
Petrova, T. D., Savchenko, T. I., Yakobson, G. G.: Zh. Obshch. Khim. 37, 1171 (1967)
Petrov, V. P., Barkhash, V. A., Shchegoleva, G. S., Petrova, T. D., Savchenko, T. I., Yakobson, G. G.: Dokl. Akad. Nauk SSSR 178, 864 (1968)
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1985 Springer-Verlag Berlin, Heidelberg
About this chapter
Cite this chapter
Furin, G.G., Grebenshchikova, G.F., Lvova, A.Y., Vlasov, V.M., Yakobson, G.G. (1985). Fluoroaromatic Compounds. In: Knunyants, I.L., Yakobson, G.G. (eds) Syntheses of Fluoroorganic Compounds. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-70207-5_3
Download citation
DOI: https://doi.org/10.1007/978-3-642-70207-5_3
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-70209-9
Online ISBN: 978-3-642-70207-5
eBook Packages: Springer Book Archive