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7 References
Methoden der Organischen Chemie, “Houben-Weyl” 4. edit. (ed. E. Müller), vol. VIc, part 1 and 2 (1976) Stuttgart, G. Thieme Verlag (cited later on only “Houben-Weyl”)
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see also Hennion, G. F., Anderson, G. J.: ibid. 68, 424 (1946)
Swanholm, U., Parker, V. D.: J. Chem. Soc. Perkin I, 1973, 562
Müller, E., Ley, K., Kiedaisch, W.: Chem. Ber. 87 1605 (1954)
Schlömer, K.: Dissertation Univ. Marburg 1959
Cook, C. D.: J. Org. Chem. 18, 261 (1953)
Müller, E., Ley, K.: Z. Naturforsch. 8b, 694 (1953)
Kalk, F.: Dissertation Univ. Marburg 1959 and unpublished results
Dimroth, K., Kalk, F., Neubauer, G.: Chem. Ber. 90, 2058 (1957)
Steuber, F. W., Dimroth, K.: ibid. 99, 258 (1966)
Steuber, F. W.: Dissertation Univ. Marburg 1963. For a similar study with 2,6-di-t-butylated phenols see Šebesta, F., Petránek, J.: Coll. Czech. Chem. Commun. 35, 2136 (1970)
Cook, C. D., et al.: J. Am. Chem. Soc. 75, 6242 (1953); ibid. 81, 1176 (1959); J. Org. Chem. 29, 3716 (1964)
Müller, E., et al.: Chem. Ber. 87, 922 (1954); Liebigs Ann. Chem. 730, 67 (1969); see also Speiser, B., Rieker, A.: J. Electroanalyt. Chem. 102, 373 (1979)
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Coppinger, G. M.: J. Am. Chem. Soc. 79, 501 (1957); Tetrahedron 18, 61 (1962)
Kharasch, M. S., Joshi, B. S.: J. Org. Chem. 22, 1435, 1439 (1957), ibid. 27, 651 (1962)
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Pokhodenko, W. D., Kalibatschuk, N. N., Khizny, W. A.: Liebigs Ann. Chem. 743, 192 (1971)
Reviews of phenoxyl radicals: a. Altwicker, E. R.: Chem. Rev. 67, 475 (1967)
Forrester, A. R., Hay, J. M., Thomson, R. H.: Organic Chemistry of Stable Radicals Chapter 7; Academic Press London and New York 1968
Pokhodenko, V. D., Khizhnyi, V. A., Bidzilya, V. A.: Russ. Chem. Rev. (engl.) 37, 435 (1968)
Strigun, L. M., Vartanyan, L. S., Emanuel, N. M.: Russ. Chem. Rev. (engl.) 37, 421 (1968)
Pokhodenko, V. D.: Phenoxyl Radikals (russ.) Dumka Verlag Kiev 1969
Ershov, V. V., Volod'kin, A. A., Prokof'ev, A. I., Solodovnikov, S. P.: Russ. Chem. Rev. (engl.) 42, 740 (1973)
Vartanyan, L. S.: Russ. Chem. Rev. (engl.) 44, 859 (1975)
Hopff, H., Haer, A.: Chimia 12, 105 (1959); AgBF4-synthesis of acetophenone at 70–80° in 1,2-dichloromethane (23% yield): Crist, D. R., Hsieh, Z.-U., Chuicksall, C. O., Sun, M. K.: J. Org. Chem. 49, 2478 (1984)
Vorländer, D., Fischer, E., Wille, H.: Ber. Dtsch. Chem. Ges. 62, 2836 (1929)
Dimroth, K., Bräuninger, G.: Angew. Chem. 68, 519 (1956)
Dimroth, K., Bräuninger, G., Neubauer, G.: Chem. Ber. 90, 1634 (1957)
for electrophilic substitution of 1,3,5-triphenylbenzene see also Ansell, H. V., Clegg, R. B., Taylor, R.: J. Chem. Soc., Perkin II 1972, 766
Dimroth, K., Neubauer, G.: Angew. Chem. 69, 95 (1957)
Kohler, E. P., Blanchard, Jr., L. W.: J. Am. Chem. Soc. 57, 367 (1935)
Saure, M.: Dissertation Univ. Marburg 1959 and unpublished results
Lewis, G.: J. Org. chem. 30, 2798 (1965); ibid. 31, 749 (1966)
Nowack, R.: unpublished results, Univ. Marburg 1962: The sulfonic acid of 1,3,5-triphenylbenzene with conc. H2SO4 in SO2 at −30–60 °C is the 4′-sulfonic acid, m.p. 84–85, giving the phenol 4′-hydroxy-1,3,5-benzene, m.p. 154–156 °C in molten KOH at 350 °C
Dimroth, K.: Angew. Chem. 72, 331 (1961)
Dimroth, K., Wolf, K. H.: Newer Methods of Preparative Organic Chemistry, Vol. III, 357 (1964) (ed. W. Forest), Academic Press New York
Reviews: Balaban, A. T., Schroth, W., Fischer, G.: Adv. Heterocycl. Chem. 10, 241 (1969)
Balaban, A. T., Dinculescu, A., Dorofeenko, G., Fischer, G., Koblik, A., Mezheritskii, M., Schroth, W.: ibid. Suppl. 2 (1982)
Reviews: Wedemeyer, K. F.: see lit. 1), 1e, 4–84
Rawlinson, D. J., Sosnovski, G.: Synthesis 1972, 1–28; ibid. 1973, 567–603
for methoxylation of arenes see Konz, E., Pistorius, R.: ibid. 1979, 603
Groebel, B. T., Konz, E., Millauer, M., Pistorius, R.: ibid. 1979, 605
see e.g. Williams, G. H.: Homolytic Aromatic Substitution Pergamon Press Oxford 1960
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Eberson, L., Jönsson, L., Wistrand, L. G.: Tetrahedron 38, 1087 (1982)
Eberson, L.: Adv. Phys. Organ. Chem. 18, 79 (1982)
see also Enisov, E. T., Metelitsa, D. I.: Russ. Chem. Rev. (engl.) 37, 656 (1968)
Ross, S. D., Finkelstein, M., Petersen, R. C.: J. Am. Chem. Soc. 86, 4139 (1964)
Leung, M., Herz, J., Salzberg, H. W.: J. Org. Chem. 30, 310, 2873 (1975)
Adams, R. N.: Acc. Chem. Res. 2, 175 (1969)
Lund, H.: Acta Chem. Scand. 11, 1323 (1957)
Eberson, L., Nyberg, K.: ibid. 18, 1568 (1966) and lit. 36)
Eberson, L., Nyberg, K.: J. Am. Chem. Soc. 88, 1686 (1966); Eberson, L.: ibid. 89; 4669 (1967)
Blum, Z., Cedheim, L., Nyberg, K.: Acta Chem. Scand. B 29, 715 (1975)
So, Y. H., Miller, L. L.: Synthesis 1976, 468
Lau, W., Huffman, J. C., Kochi, J. K.: J. Am. Chem. Soc. 104, 5515 (1982); see also lit. 41)
Heiba, E. I., Dessau, R. M., Koehl Jr., W. J.: J. Am. Chem. Soc. 91, 6830 (1969)
Kochi, J. K., Tang, R. T., Bernath, T.: ibid. 95, 7114 (1973) and lit. cit. therein
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for catalysis see Eberson, L.: J. Mol. Catalys. 20, 27 (1983)
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Kozyrod, R. P., Pinhey, J. T.: ibid. 23, 5365 (1982) and lit. cit. therein
Eberson, L., Gomez-Gonzalez, L.: Acta Chem. Scand. 27, 1249 (1973)
for similar acetoxylations see Eberson, L., Jönssen, L.: J. Chem. Soc. Chem. Commun. 1974, 885
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Itahara, T.: Chem. and Ind. (London) 1982, 599
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Rüchardt, C., Merz, E.: Tetrahedron Letters 1964, 2431
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Dimroth, K., Schromm, K.: unpublished results 1962
Kozyrod, R. P., Pinhey, J. T.: Tetrahedron Lett. 23, 1982, 5365 (1982)
Craig, H. C., Pinhey, J. T., Sternhell, S.: Aust. J. Chem. 32, 1551 (1979)
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Wolf, W., Kharasch, N.: J. Org. Chem. 30, 2493 (1965)
Photoarylation see also Soumillion, J. P., De Wolf, B.: Chem. Commun 1981, 436
for iodophenolether synthesis see Burger, A., Wilson, E. L., Brindley, C. O., Bernheim, F.: J. Am. Chem. Soc. 67, 1416 (1945)
Ugochukwu, E. N., Wain, R. L.: Chem. and Ind. (London) 1965, 35
Schminke, H. D.: Dissertation Univ. Marburg 1961
Güsten, H., Kirsch, G., Schulte-Frohlinde, D.: Tetrahedron 24, 4393 (1968)
Hay, A., Clark, R. F.: Makromolecules 3, 533 (1970)
Gerard, W., Lappert, M. F.: Chem. Rev. 58, 1081 (1958)
Schäfer, W., Franck, K.: Chem. Ber. 99, 160 (1966)
McOmie, J. F., Watts, M. L., West, D. E.: Tetrahedron 24, 2289 (1968)
Adams, R., Mathieu, J.: J. Am. Chem. Soc. 70, 2120 (1948)
Prey, V.: Ber. Dtsch. Chem. Ges. 74, 1219 (1941); ibid. 75, 445 (1942); ibid. 76, 156 (1943)
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Kolka, A. J., Napolitano, J. P., Filbey, A. H., Ecke, G. G.: ibid. 22, 642 (1957)
Smith, W., Sommerfield, E. H.: USP 4001340; C. A. 86, 120796 (1977)
Britton, E. C.: USP 159283, (1931); C. 1934, II, 1688; USP 196744 (1932); C. 1935, II, 1962
Moose, J. E.: USP 1979116 (1932); C 1935, I, 3200
Lüttringhaus, A., v. Sääf, G.: Angew. Chem. 51, 915 (1938); Liebigs Ann. Chem. 542, 241 (1939); 557, 25 (1947)
Lüttringhaus, A., Ambros, D.: Chem. Ber. 89, 463 (1956)
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Gross, D. E., Fishel, N. A.: USP 4000203; C. A. 86, 89385 (1977)
Gross, D. E.: USP 3989761; C. A. 86, 72193 (1977)
Fishel, N. A., Gross, D. E.: USP 4035428; C. A. 87, 134 589 (1977)
Fishel, N. A., Anvil, S. R., Gross, D. E.: Catalog Org. Synth. 1978, 119 (7th ed.)
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Kagaku, S.: Jap. P. 81,20533, C. A. 95, 42640 91981)
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see also Squires, T. G., Vernier, C. G., Hodgson, B. A., Chung, L. W., Davies, V. A., Panuto, T. W.: J. Org. Chem. 46, 2373 (1981)
Bunnett, J. F., Zahler, R. E.: Chem. Rev. 49, 273 (1951)
Davies, D. I., Hey, D. H., Williams, G. H.: J. Chem. Soc. (London) 1961, 562
Hawthorne, M. F.: J. Org. Chem. 22, 1001 (1957)
Kuivila, H. G.: J. Am. Chem. Soc. 76, 870 (1954)
Yarboro, T. L., Karr, C.: J. Org. Chem. 24, 1141 (1959)
Eberson, L., Jönsson, L., Wistrand, L.-G.: Tetrahedron 38, 1087 (1982) and lit. cit. therein
Eberhardt, M. K.: J. Org. Chem. 42, 832 (1977); J. Phys. Chem. 81, 1051 (1977)
Zoratti, M., Bunnett, J. M.: J. Org. Chem. 45, 1769 (1980)
Bunnett, J. F.: Acc. Chem. Res. 11, 413 (1978)
Kornblum, N.: Angew. Chem. 87, 797 (1975); Angew. Chem. engl. 14, 734 (1975)
Russell, G. A., Danen, W. C.: J. Am. Chem. Soc. 90, 347 (1968) and later publications
Cerfontain, H.: J. Org. Chem. 47, 4680 (1982)
Suzumura, H.: Bl. chem. Soc. Japan 35, 108 (1962)
Hay, A. S., Clark, R. F.: Makromolecules 3, 533 (1970)
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Plešek, J.: Chem. Listy 50, 246 (1956); C.A. 50, 7732 (1956) Coll. Czech. Chem. Commun. 21, 275 (1956)
Munk, P., Plešek, J.: Chem. Listy 51, 771 (1957); C.A. 51, 11261 (1957)
Plešek, J., Munk, P.: ibid. 51, 633 (1957)
Munk, P., Plešek, J.: ibid 51, 771 (1957); C.A. 51, 11261 (1957)
see also Kunze, H.: Ber. dtsch. Chem. Ges. 59, 2085 (1926)
de Jonge, C. R. H. I., van Dort, H. M., Vollbracht, L.: Tetrahedron Lett. 1970, 1881
Hay, A. S.: Brit. P. 1207524 (1967); C.A. 77, 126220 (1967)
Kapner, R. S., Kippax, D. L., Murphy, K. E., Udani, H. H.: Germ. P. 163402; C.A. 83, 163813 (1975)
see also Brit. P. 1207524; C.A. 77, 126220 (1972)
Hay, A. S.: see lit. 61; Boon, J., Mayer, E. P.: J. Polymer Sci. 7, 205 (1969)
Schwarz, H. H., Metten, J., Koeller, H. Tacke, P., Weissel, O.: Germ. Offen 2.102746 (1971); C.A. 77 126218 (1972)
Naarman, H., Brandstetter, F., Schuster, H. H.: Europ. Appl. P. EP 47824; C.A. 96, 218455, 218418 (1982)
Hay, A. S., Blanchard, H. S., Endres, G. F., Eustance, J. W.: J. Am. Chem. Soc. 81, 6335 (1959)
see also Hay, A. S.: J. Org. Chem. 27, 3320 (1962); the Cu(I) complex is also very valuable for oxidative acetylene coupling
Hay, A. S.: Tetrahedron Lett. 1965, 4241
Winnacker-Küchler: Chemische Technologie, 4. ed., vol. 6, Carl Hanser Verlag, München 1982
Hay, A. S.: Advances Polymer Sci. 58, 581 (1962)
Endres, G. F., Hay, A. S., Eustance, J. W.: J. Org. Chem. 28, 1300 (1963)
X-ray of two cristalline poly-2,6-diphenyl-4-phenyl-oxydes see Boon, J., Magré, E. P.: Macromol. Chem. 136, 267 (1970)
Davies, G., El Sayed, M. A., Fasano, R. E.: Inorg. Chim. Acta 71, 95 (1983) and lit. cited therein
Capdevielle, P., Maumy, M.: Tetrahedron Lett. 24, 5611 (1983)
King, F. D., Walton, D. R. M.: Synthesis 1976, 40
Pinhey, J. T., Rowe, B. A.: Aust. J. Chem. 33, 113 (1980)
for other routes of α-arylation of ketons see: Bunnett, J. F., Sundberg J. E.: J. Org. Chem. 41, 1702 (1976) of potassium cyclohexanenolate in liquid ammonia with PhBr in benzene and light (350 nm) according to a SRN1 chain mechanism (72% 2-phenylcyclohexanone)
Meerwein-α-arylation of cyclohexene-enolether or enolacetate with aryldiazonium salt and Cu(I) salts; Allard, M. N., Levisalle, J.: Bull. soc. chim. France 1972, 1926; Adel, Al., Salami, B. A., Levisalles, J., Rudler, H.: ibid. 1976, 930
LiCuPh2 and p-tolyazocyclohexene: Sacks, C. E., Fuchs, P. L.: J. Am. Chem. Chem. Soc. 97, 7372 (1975)
McKillop, A., Rao, D. P.: Syntheses 1977, 759
Krapcho, A. P., Lovey, A. J.: Tetrahedron Lett. 1973, 957
Barton, D. H. R., Papoula, H. T. B., Guilhem, J., Motherwell, W. B., Pascard, C., Huu Dau, E.: J. Chem, Soc. Chem. Commun. 1982, 732
Barton, D. H. R., Lester, D. J. L., Motherwell, W., Papoula, M. T.: ibid. 1980, 246
Pinhey, J. T., Rowe, B. A.: Aust. J. Chem. 36, 789 (1983)
Horning, E. C., Horning, M. C.: J. Am. Chem. Soc. 69, 1359 (1947)
Woods, G. F., Tucker, I. W.: ibid 70, 2174 (1948)
Review: Posner, G. H.: Organic Reactions 19, 1 (1972)
Malmberg, H., Nilsson, M., Ullenius, C.: Tetrahedron Lett. 23, 3823 (1982); Review: Normant, J. F.: Synthesis 1972, 63
Woods, G. F., Reed, F. T., Arthur, T. E., Ezekiel, H.: J. Am. Chem. Soc. 73, 3854 (1951)
Petrow, A. D.: Ber. dtsch. Chem. Ges. 62, 642 (1929) and cited lit.; ibid. 63, 898 (1930)
Kenner, J., Shaw, H.: J. Chem. Soc. (London) 1931, 769
Sexsmith, D. R., Rassweiler, J. H.: J. Org. Chem. 25, 1229 (1960); see also lit. 99)
Downes, A. M., Gill, N. S., Lions, F.: J. Am. Chem. Soc. 72, 3464 (1951); for similar syntheses see b) Nasipuri, D., Roy Choudbury, S. R., Blattacharya, A.: J. Chem. Soc. Perkins I, 1973, 1451
Egli, C., Helali, S. E., Hardegger, E.: Helv. Chim. Acta 58, 104 (1975)
Zimmerman, H. E., Schuster, D. I.: J. Am. Chem. Soc. 84, 4527 (1962)
for the syntheses of the 3,6-diphenyl-and 2,3-6-triphenyl-cyclohex-2-enones see Abdullah, S. M.: J. Ind. Chem. Soc., 12, 62 (1935); C. 1935 I, 3926
Hill, H. B.: Am Chem. J. 22, 89 (1899); 24, 5 (1900); Ber. dt. Chem. Ges. 33, 1241 (1900); see also Borsche, W.: Liebigs Ann. Chem. 312, 211 (1900)
Yates, P., Hyre, J. E.: J. Org. Chem. 27, 4101 (1962)
for the synthesis of 2,3,4,6-and 2,3,5,6-tetraphenyl-phenol see also Eistert, B., Langbein, A.: Liebigs Ann. Chem. 678, 78 (1964)
Eicher, T., v. Angerer F. Lichigs Ann. 746, 120 (1971)
Ried, W., König, E.: ibid. 757, 153 (1972)
see also Perst, H., Wesemeyer, I.: Tetrahedron Lett. 1970, 4189
Suter, C. M., Smith, P. G.: J. Am. Chem. Soc. 61, 166 (1939)
Ames, G. R., Davey, W.: J. Chem. Soc. London, 1957, 3480, 1958, 1794
Betts, B. E., Davey, W.: ibid, 1961, 1683, 3440
see also Fichter, F., Grether, E.: Ber. dtsch. Chem. Ges. 36, 1407 (1903)
Harrison Jr., E. A.: J. Org. Chem. 44, 1807 (1979)
Ueji, S., Nakatsu, K., Yoshioka, H., Kinoshita, K.: Tetrahedron Lett. 1982, 1173
Jones, E. C. S., Kenner, J.: J. chem. Soc. (London) 1931, 769; 1842
Hay, A. S.: J. Org. Chem. 30, 3577 (1965)
Bordwell, F. G., Wellmann, K. M.: ibid. 29, 509 (1964)
Worschech, K.: Dissertation Univ. Marburg 1960; see also lit. 137)
Kvalnes, D. E.: J. Am. Chem. Soc. 56, 2478 (1934)
Zimmerman, H. E.: Angew. Chem. 81, 45 (1969); engl. 8, 1
Zimmerman, H. E., Epling, G. A.: J. Am. Chem. Soc. 94, 7806 (1972)
Dannenberg, W., Lemmer, D., Perst, H.: Tetrahedron Lett. 1974, 2133
Dannenberg, W.: Dissertation Univ. Marburg 1975
Rau, W.: Dipl. Arb. Univ. Marburg 1980
the mechanism of these and similar rearrangements has been fully studied by Perst and coworkers, see e.g. Perst, H.: Habil. Arbeit, Univ. Marburg 1972
Dannenberg, W., Perst, H.: Liebigs Ann. Chem. 1975, 1873
Dannenberg, W., Perst, H., Seifert, W. J.: Tetrahedron Lett. 1975, 3481
Weisskopf, V., Perst, H.: Liebigs Ann. 1978, 1634
Monahan, A. S.: J. Org. Chem. 33, 1441 (1968)
Eistert, B., Langbein, A.: Liebigs Ann. Chem. 678, 78 (1964)
Eistert, B., Thommen, A. J.: Chem. Ber. 104, 3048 (1971)
Dürr, H., Heilkämper, P.: Liebigs Ann. Chem. 716, 212 (1968)
Hart, H. Raggon, J. W.: Tetrahedron Lett. 24, 4891 (1983)
Evans, D. A., Hoffmann, J. M., Truesdale, L. K.: J. Am. Chem. Soc. 95, 5822 (1973)
Evans, D. A., Hart, D. J., Koelsch, P. M., Chain, P. A.: Pure and Appl. Chem. 51, 1285 (1979) and lit. cit. therein
see also Parker, K. A., Kang, S.-K.: J. Org. Chem. 45, 1218 (1980)
Liotta, D., Saindane, M., Barnum, C.: J. Org. Chem. 46, 3369 (1981)
Fischer, A., Henderson, G. N.: Tetrahedron Lett. 24, 131 (1983) and lit. cit. therein
Rieker, A., Hernes, G.: Tetrahedron Lett. 1968, 3775
Rieker, A.: Angew. Chem. 81, 938 (1969); engl. 8, 918 (1969)
Dimroth, K., Berndt, A., Volland, R.: Chem. Ber. 99, 3040 (1966)
Berndt, A.: Dissertation Univ. Marburg 1965
Dimroth, K., Vogel, K., Krafft, W.: Chem. Ber. 101, 2215 (1968)
Michel, W.: Dissertation Univ. Marburg 1961
Müller, E., Schick, A., Scheffler, K.: Chem. Ber. 92, 474 (1959)
Müller, E., Schick, A., Mayer, R., Scheffler, K.: ibid. 93, 2649 (1960)
Dimroth, K., Berndt, A., Reichardt, C.: Organic Synthesis, Coll. Vol. 5, 1128 (1973)
Dimroth, K., Berndt, A., Perst, H., Reichardt, C.: ibid. p. 1130
Dimroth, K., Reichardt, C., Vogel, K.: ibid. p. 1135
Blöcher, K. H.: Dissertation Univ. Marburg 1961
Dimroth, K., Kalk, F. Sell, R., Schlömer, K.: Liebigs Ann. Chem. 624, 51 (1959)
Dimroth, K., Wolf, K. H.: Angew. Chem. 72, 777 (1960)
Dimroth, K., Umbach, W., Blöcher, K. H.: Angew. Chem. 75, 860 (1963); Angew. Chem. engl. 2, 620 (1963) and unpublished results of Umbach, W.
Lendenfeld, H.: Monatsh. 27, 969 (1906); Ariyan, Z. S., Mooney, B.: J. Chem. Soc. (London) 1962, 1519
Wache, H.: Dissertation Univ. Marburg 1964
Dimroth, K., Wache, H.: Chem. Ber. 99, 399 (1966)
Laubert, G.: Dissertation Univ. Marburg 1968
Dimroth, K., Laubert, G., Blöcher, K. H.: Liebigs Ann. Chem. 765, 133 (1972)
Güsten, H., Kirsch, G., Schulte-Frohlinde, D.: Angew. Chem. 79, 941 (1967); engl. 6, 948 (1967); Tetrahedron 24, 4393 (1968)
Dimroth, K., Schromm, K.: unpublished results 1962
Nelsen, St. F.: in Free Radicals, (ed. J. K. Kochi) vol. II, 527, John Wiley and Sons, New York, London Sidney, Toronto (1973)
Griller, D., Barclay, L. R., Ingold, K. U.: J. Am. Chem. Soc. 97, 6151 (1975) and lit. cited therein
see also Chattaway, F. D., Orton, K. J. P.: J. Chem. Soc. (London) 79, 461 (1901)
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Dimroth, K. (1985). Arylated phenols, aroxyl radicals and aryloxenium ions syntheses and properties. In: Photochemistry and Organic Synthesis. Topics in Current Chemistry, vol 129. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-15141-9_3
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