Oxidation of Organic Compounds with Nickel Peroxide

  • M. V. George

Abstract

Although it has been known for a long time that nickel peroxide could be used for oxidizing organic compounds, only in the last few decades or so has this reagent found extensive application in synthetic organic chemistry. Weijlard1 reported that diacetone-2-keto-levo-gulonic acid, an intermediate in the synthesis of vitamin C, was obtained from diacetone-levo-sorbose in good yields by the addition of nickel salts in a solution of sodium hypochlorite. It was suggested that the black oxide of nickel formed by the treatment of sodium hypochlorite with nickel sulfate was responsible for this type of oxidation. In recent years nickel peroxide has been used more frequently for bringing about the oxidations of several types of organic compounds.2, 3

Keywords

Hydrazine Allyl Furfural Hydrazide Acetophenone 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J. Weijlard, Hypochlorites in organic oxidations, J. Am. Chem. Soc. 67, 1031–1032 (1945).CrossRefGoogle Scholar
  2. 2.
    M. V. George and K. S. Balachandran, Nickel peroxide oxidation of organic compounds, Chem. Rev. 75, 491–519 (1975).CrossRefGoogle Scholar
  3. 3.
    K. Nakagawa, R. Konaka, and J. Sugita, Application and mechanism of oxidation with nickel peroxide, Shionogi Kenkyusho Nempo 19, 141–161 (1969); Chem. Abstr. 72, 16048a (1970).Google Scholar
  4. 4.
    W. F. Pickering, Heterogenous oxidation reactions, Rev. Pure Appl. Chem. 16, 185–208 (1966); Chem. Abstr. 66, 98882z (1967).Google Scholar
  5. 5.
    K. Nakagawa, The application of nickel peroxide oxidation in organic synthesis, Tokushima Bunri Daigaku Kenkyu Kiyo 20, 65–75 (1980); Chem. Abstr. 93, 237962y (1980).Google Scholar
  6. 6.
    K. Nakagawa, R. Konaka, and T. Nakata, Oxidation with nickel peroxide. I. Oxidation of alcohols, J. Org. Chem. 27, 1597–1601 (1962).CrossRefGoogle Scholar
  7. 7.
    R. N. Warrener and E. N. Cain, Nickel peroxide as a selective oxidant in the pynmidine series. The synthesis of Nl-substituted orotic and 2-thioorotic acids, Aust. J. Chem. 24, 785–807 (1971).CrossRefGoogle Scholar
  8. 8.
    A. E. Feiring, Chemistry in hydrogen fluoride 6. Oxidative fluorination of aromatic compounds, J. Org. Chem. 44, 1252–1254 (1979).CrossRefGoogle Scholar
  9. 9.
    A. E. Feiring, Oxidative fluorination of aromatic compounds in liquid hydrogen fluoride, J. Fluorine Chem. 10, 375–386 (1977); Chem. Abstr. 88, 89230n (1978).CrossRefGoogle Scholar
  10. 10.
    M. Hajek and J. Malek, Radical addition of nitrites to 1-alkenes initiated by metal oxides. Collection Czechoslov. Chem. Commun. 42, 2388–2393 (1977).Google Scholar
  11. 11.
    R. Konaka, S. Terabe, and K. Kuruma, Mechanism of the oxidation reaction with nickel peroxide, J. Org. Chem. 34, 1334–1337 (1969).CrossRefGoogle Scholar
  12. 12.
    H. G. Aurich and F. Baer, Nitroxide II. Die oxidation von Derivaten des phenylhydroxylamines, Tetrahedron Lett. 1965, 3879–3883.Google Scholar
  13. 13.
    R. Konaka, and K. Kuruma, A mechanistic study of 1,2-glycol cleavage with nickel peroxide, J. Org. Chem. 36, 1703–1704(1971).CrossRefGoogle Scholar
  14. 14.
    S. Terabe and R. Konaka, Electron spin resonance studies on oxidation with nickel peroxide. Spin trapping of free radical intermediates, J. Am. Chem. Soc. 91, 5655–5657 (1969).CrossRefGoogle Scholar
  15. 15.
    S. Terabe, K. Kuruma, and R. Konaka, Spin trapping by use of nitroso compounds. III. Phenoxazine-JV-oxyl produced from the phenoxy radical by spin trapping, Chem. Lett. 1972, 115–118; Chem. Abstr. 76, 113143m (1972).Google Scholar
  16. 16.
    S. Terabe and R. Konaka, Spin trapping by use of nitroso compounds. Part IV. Electron spin resonance studies on oxidation with nickel peroxide, J. Chem. Soc. Perkin II 1972, 2163–2172.Google Scholar
  17. 17.
    K. Nakagawa, K. Igano, and J. Sugita, Oxidation with nickel peroxide III. Oxidative cleavage of a-glycols, a-hydroxy acids, a-oxo alcohols and ot-oxo acids, Chem. Pharm. Bull. (Tokyo) 12, 403–407 (1964); Chem. Abstr. 61, 1789 (1964).Google Scholar
  18. 18.
    R. Criegee, E. Buchner, and W. Walther. Die geschwindigkeit der glykolspaltung mit Blei IV-acetat in abhangigkeit von der Konstitution des glykols, Chem. Ber. 73, 571–575 (1940).Google Scholar
  19. 19.
    H. Kwart and T. J. George, Primary deuterium isotope effects in oxidations of benzyl-a-d alcohol by transition elements and related reagents: Mechanisms of electron transfer, J. Org. Chem. 44, 162–164 (1979).CrossRefGoogle Scholar
  20. 20.
    J. Sugita, Reaction of alkylphenols with nickel peroxide, Nippon Kagaku Zasshi 87, 603–607 (1966); Chem. Abstr. 65, 15522c (1966);CrossRefGoogle Scholar
  21. 21.
    J. Sugita, Reaction of alkylphenols with nickel peroxide, Nippon Kagaku Zasshi 87, 607–609 (1966); Chem. Abstr. 65, 15522e (1966).CrossRefGoogle Scholar
  22. 22.
    J. C. Leflingwell, The oxidative coupling of aliphatic aldehydes, Chem. Commun. 1970, 357–358.Google Scholar
  23. 23.
    J. Sugita, Reaction of diphenylamines with nickel peroxide, Nippon Kagaku Zasshi 88, 1235–1237 (1967); Chem. Abstr. 69, 2619g (1968).CrossRefGoogle Scholar
  24. 24.
    K. S. Balachandran, I. Bhatnagar, and M. V. George, Oxidation by metal oxides. IV. Oxidation of organic compounds using nickel peroxide, J. Org. Chem. 33, 3891–3895 (1968).CrossRefGoogle Scholar
  25. 25.
    I. Bhatnagar and M. V. George, Oxidation with metal oxides. II. Oxidations of chalcone phenylhydrazones, pyrazolines, o-aminobenzylidine anils and o-hydroxybenzylidine anils with manganese dioxide. Tetrahedron 24, 1293–1298 (1968).CrossRefGoogle Scholar
  26. 26.
    K. Nakagawa, H. Onoue, and K. Minami, Oxidation with nickel peroxide. VI. Oxidation of N-substituted hydroxylamine derivatives with nickel peroxide, Chem. Pharm. Bull. (Tokyo) 17, 835–837 (1969); Chem. Abstr. 71, 60896x (1969).Google Scholar
  27. 27.
    R. J. Gritter and T. J. Wallace, The manganese dioxide oxidation of allylic alcohols J. Org. Chem. 24, 1051–1056(1959).CrossRefGoogle Scholar
  28. 28.
    M. Harfenist, A. Bavley, and W. A. Lazier, The oxidation of allyl and benzyl alcohols to the aldehydes, J. Org. Chem. 19, 1608–1616 (1954);CrossRefGoogle Scholar
  29. 29.
    S. Ball, T. W. Goodwin, and R. A. Morton, Studies on vitamin A. V. Preparation of retinenevitamin A aldehyde, Biochem. J. 42, 516–523 (1948); Chem. Abstr. 42, 8916f (1948).Google Scholar
  30. 30.
    L. D. Gavrilov, M. I. Klopotova, and L. I. Vereshchagin, Unsaturated carbonyl containing compounds. XIV. Oxidation of acetyienic alcohols and glycols by nickel peroxide, Zh. Org. Khim. 10, 2064–2067 (1974); Chem. Abstr. 82, 72726g (1975).Google Scholar
  31. 31.
    S. Mineo and K. Nakagawa, Oxidation with nickel peroxide. VII. Preparation of a-diketones from a-ketoalcohols, Yakugaku Zasshi 94, 1180–1182 (1974); Chem. Abstr. 81, 169250q (1974).Google Scholar
  32. 32.
    M. Bertrand, G. Gil, and J. Viala, Convenient route to a-allenic aldehydes, ketones and amides, Tetrahedron Lett. 1979, 1595–1598.Google Scholar
  33. 33.
    E. J. Corey and J. W. Suggs, Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett. 1975, 2647–2650.Google Scholar
  34. 34.
    H. Musso, Phenol oxidation reactions, Angew. Chem. Internat. Ed. Engl. 2, 723–735 (1963).CrossRefGoogle Scholar
  35. 35.
    J. Sugita, Reaction of 2, 6-disubstituted phenols with nickel peroxide, Nippon Kagaku Zasshi 87. 607–609 (1966); Chem. Abstr. 65, 15222c (1966).CrossRefGoogle Scholar
  36. 36.
    J. Sugita. Reaction of /cr/-butylphenols with nickel peroxide, Nippon Kagaku Zasshi 87, 1082–1088 (1966); Chem. Abstr. 66, 94777w (1967).CrossRefGoogle Scholar
  37. 37.
    M. F. Ansell and A. F. Gosden. The Diels-Alder reaction of obenzoquinones. Chem. Commun. 1965, 520–521.Google Scholar
  38. 38.
    H. D. Becker, The preparation of fuchsones, J. Org. Chem. 32, 2943–2947 (1967).CrossRefGoogle Scholar
  39. 39.
    E. G. E. Hwkins and R. Large, Dehydrodimerization of ketones by nickel peroxide, J. Chem. Soc. Perkin I 1974, 280–284.CrossRefGoogle Scholar
  40. 40.
    K. Nakagawa, H. Onoue, and K. Minami, Oxidation with nickel peroxide. A new synthesis of amides from aldehydes or alcohols. Chem. Commun. 1966. 17–18.Google Scholar
  41. 41.
    K. Nakagawa, H. Onoue, K. Minami, and S. Mineo, Oxidation with nickel peroxide. IX. Synthesis of amides by ammoxidation of aldehydes, Yakugaku Zasshi 95, 1167–1172 (1975); Chem. Abstr. 84, 301221 (1976).Google Scholar
  42. 42.
    K. Nakagawa and T. Tsuji, Oxidation with nickel peroxide. II. Oxidation of amines, Chem. Pharm. Bull. (Tokyo) 11, 296–301 (1963); Chem. Abstr. 59, 3827b (1963).Google Scholar
  43. 43.
    M. Z. Barakat, M. F. Abdel-Wahab, and M. M. El-Sadr, Oxidation of organic compounds by solid manganese dioxide, J. Chem. Soc. 1956, 4685–4687.Google Scholar
  44. 44.
    K. Nakagawa and H. Onoue, Oxidation with nickel peroxide. V. The formation of cis, cis-1, 4 -dicyano-l,3-butadienes in the oxidation of o-phenylenediamines, Tetrahedron Lett. 1965, 1433–1436.Google Scholar
  45. 45.
    I. Bhatnagar and M. V. George, Oxidation with metal oxides. III. Oxidation of diamines and hydrazines with manganese dioxide, J. Org. Chem. 33, 2407–2411 (1968).CrossRefGoogle Scholar
  46. 46.
    J. Sugita. Oxidation with nickel peroxide. V. Reaction of carbazoles with nickel peroxide, Nippon Kagaku Zasshi 88, 659–667 (1967); Chem. Abstr. 69, 10319z (1968).Google Scholar
  47. 47.
    H. B. Henbest and A. Thomas, Manganese dioxide oxidation of some tertiary amines, Chem. Ind. 1956, 1097.Google Scholar
  48. 48.
    E. F. Pratt and T. P. McGovern, Oxidation by solids. III. Benzalanilines from N-benzoylanilines and related oxidations by manganese dioxide, J. Org. Chem. 29, 1540–1543 (1964).CrossRefGoogle Scholar
  49. 49.
    B. T. Golding and D. R. Hall, Formation of derivatives of cyclopropane by an oxidative cyclization using nickel peroxide, Chem. Commun. 1970, 1574–1575.Google Scholar
  50. 50.
    H. Ohta and K. Tokumaru, Use of nickel peroxide as oxidizing agent of phenylhydrazine for the generation of phenyl radicals, Bull. Chem. Soc. Jpn. 44, 3478–3479 (1971); Chem. Abstr. 76, 59096h (1972).CrossRefGoogle Scholar
  51. 51.
    K. S. Balachandran and M. V. George, Oxidation with metal oxides. Part VIII. Oxidation of SchifT bases, hydrazines and amines with nickel peroxide, lnd. J. Chem. 11, 1267–1271 (1973).Google Scholar
  52. 52.
    K. Nakagawa, H. Onoue, and K. Minami, Oxidation with nickel peroxide. The preparation of diazo-compounds from hydrazones, Chem. Commun. 1966, 730–731.Google Scholar
  53. 53.
    Wm. Schroeder, Diaryldiazomethane, U. S. Patent No. 2,710,862 (1965); Chem. Abstr. 50, 6510h (1956).Google Scholar
  54. 54.
    R. Kalish and W. H. Pirkle, Synthesis of allenes by means of cycloelimination reactions, J. Am. Chem. Soc. 89, 2781–2782 (1967).CrossRefGoogle Scholar
  55. 55.
    S. Mineo, H. Ogura, and K. Nakagawa, Studies on heterocyclic compounds. XXXII. Synthesis of 8-substituted theophyllines with 6-amino-5-benzylideneamino-l, 3-dimethyluracils with nickel peroxide, Chem. Pharm. Bull. (Jpn) 28, 2835–2838 (1980); Chem. Abstr. 94. 121467g (1981).Google Scholar
  56. 56.
    G. Wittig and H. Heyn, Ober class intermediare Auftreten von Benzocycloheptenin und Indin, Chem. Ber. 97, 1609–1618 (1964).CrossRefGoogle Scholar
  57. 57.
    G. Wittig, Small rings with a carbon-carbon triple bond. Rev. Chim.Acad., Rep. Populaire Roumaine 7, 1393–1403 (1962); Chem. Abstr. 61, 4297c (1964).Google Scholar
  58. 58.
    G. Wittig, Small rings with carbon-carbon triple bonds, Angew. Chem. Internal. Ed. Engl. 1, 415–419 (1962).CrossRefGoogle Scholar
  59. 59.
    I. Bhatnagar and M. V. George, Oxidation of phenylhydrazones with manganese dioxide, J. Org. Chem. 32, 2252–2256 (1967).CrossRefGoogle Scholar
  60. 60.
    K. S. Balachandran, I. Hiriyakkanavar, and M. V. George, Oxidation with metal oxides. VII. Oxidation of bisphenylhydrazones of 1, 2-diketones with nickel peroxide. Tetrahedron 31, 1171–1177 (1975).CrossRefGoogle Scholar
  61. 61.
    C. S. Angadiyavar, K. B. Sukumaran, and M. V. George, Mesoionic l-phenylimino-2,4,5-triphenyl-1,2,3-triazole; A new 1,3-dipolar system. Tetrahedron Lett. 1971. 633–636.Google Scholar
  62. 62.
    K. B. Sukumaran, C. S. Angadiyavar, and M. V. George, 1,3-Dipolar cycloaddition of anhydro 1-phenylimino-2,4,5-triphenyl-l,2,3-triazolium hydroxide. Tetrahedron 28, 3987–3998 (1972).CrossRefGoogle Scholar
  63. 63.
    K. S. Balachandran and M. V. George, Oxidation with metal oxides. VI. Oxidation of ben-zoylhydrazones of aldehydes, ketones and 1,2-diketones with nickel peroxide. Tetrahedron 29, 2119–2128 (1973).CrossRefGoogle Scholar
  64. 64.
    K. Nakagawa, H. Onoue, and J. Sugita, Oxidation with nickel peroxide. IV. The preparation of ben-zoxazoles from Schiflf bases, Chem. Pharm. Bull. (Tokyo) 12, 1135–1138 (1964); Chem. Abstr. 62, 541f (1965).Google Scholar
  65. 65.
    S. Mineo, S. Kawamura, and K. Nakagawa, Oxidation with nickel peroxide. X. Oxidative cyclization of 2-picoline aldehyde and 2-pyridyl ketone hydrazones with nickel peroxide. Synth. Commun. 6, 69–74 (1976).CrossRefGoogle Scholar
  66. 66.
    K. S. Balachandran and M. V. George, Oxidation by metal oxides. IX. Oxidation of benzylidene acetone phenylhydrazones with nickel peroxide. Tetrahedron 31, 1491–1499 (1975).CrossRefGoogle Scholar
  67. 67.
    A. E. Feiring, Fluorination process, U.S. Patent No. 4,051,168; Chem. Abstr. 87, 184189u (1977).Google Scholar
  68. 68.
    J. Sugita, Oxidation with nickel peroxide. VI. Reaction of phenylacetonitnle with nickel peroxide, Nippon Kagaku Zasshi 88, 668–675 (1967); Chem. Abstr. 68, 86544u (1968).CrossRefGoogle Scholar
  69. 69.
    J. Sugita, Reaction of organic sulfur compounds with nickel peroxide, Nippon Kagaku Zasshi 88, 1237–1238 (1967); Chem. Abstr. 69, 2640g (1968).CrossRefGoogle Scholar
  70. 70.
    J. Sugita and Y. Tsujino, Reaction of phenothiazines with nickel peroxide, Nippon Kagaku Zasshi 89, 309–315 (1968); Chem. Abstr. 69, 67304v (1968).CrossRefGoogle Scholar
  71. 71.
    H. Ogura, S. Mineo, and K. Nakagawa, Studies on heterocyclic compounds. XXXV. Facile synthesis of 3-methylamino-l,2,4-triazoio[4,3-a]pyridine with nickel peroxide, Heterocvcies 14, 1125–1126 (1980).CrossRefGoogle Scholar
  72. 72.
    D. L. Evans, D. K. Minster, and U. Jordis, Nickel peroxide dehydrogenation of oxygen-, sulfur-, and nitrogen-containing heterocycles, J. Org. Chem. 44, 497–501 (1979).CrossRefGoogle Scholar
  73. 73.
    S. Takase and T. Motoyama, Studies of Diels-Alder type addition of cyclic a-carbonyi azo compounds, Bull. Chem. Soc. Jpn. 43, 3926–3927 (1970).CrossRefGoogle Scholar
  74. 74.
    C. D. Campbell and C. W. Rees, Reactive intermediates. Part III. Oxidation of 1-aminobenzotriazole with oxidants other than lead tetraacetate, J. Chem. Soc. (C) 1969, 752–756.Google Scholar
  75. 75.
    A. M. Liquori, Catalytic conversion of hydrocarbons to 3- p-menthene and p-cymene, U.S. Patent No. 3,280,207 (1966); Chem. Abstr. 66, U073h (1967).Google Scholar
  76. 76.
    T. Nakata, Radical organic synthesis with use of metal catalysts. I. Telomerization initiated by nickel peroxide, Kogyo Kagaku Zasshi 65, 1044–1048 (1962); Chem. Abstr. 58, 579 (1963).Google Scholar
  77. 77.
    A. Ujhidy, B. Babos, L. Marko, and A. Muller, Ober die isomeren Trichlorotribromathane, Chem. tor. 98, 2197–2200(1965).Google Scholar
  78. 78.
    J. Tanaka, T. Katagiri, and T. Hirabayashi, Reactions between isoprene and prenyl chloride using metal peroxides as the catalyst, Nippon Kagaku Zasshi 88, 1106–1111 (1967); Chem. Abstr. 69, 44033s (1968).CrossRefGoogle Scholar
  79. 79.
    M. Imoto, T. Otsu, T. Nakata, and Y. Kinoshita, Solid metal peroxides as radical initiator of stereospecific polymerization, J. Polymer Sci. Part B, Polymer Lett. 2, 227–230 (1964).CrossRefGoogle Scholar
  80. 80.
    T. Nakata, T. Otsu, and M. Imoto, Vinyl polymerization. CXI. Polymerization of styrene initiated by nickel peroxide, J. Polymer Sci. Part A 3. 3383–3397 (1975).Google Scholar
  81. 81.
    T. Nakata, Y. Kinoshita, T. Otsu, and M. Imoto, Vinyl polymerization. CXIV. The polymerization of styrene initiated by metal peroxides as solid radical initiators, Kogyo Kagaku Zasshi 68, 858–864 (1965); Chem. Abstr. 63, I826lg (1965).Google Scholar
  82. 82.
    T. Nakata, Y. Kinoshita, T. Otsu, and M. Imoto, Vinyl polymerization. CXV. Radical polymerization of butadiene and isoprene by nickel peroxide, Kogyo Kagaku Zasshi 68, 864–868 (1965); Chem. Abstr. 63, 18262b, c (1965).Google Scholar
  83. 83.
    T. Nakata, T. Otsu, and M. Imoto, Vinyl polymerization. CLI. The polymerization of vinyl acetate initiated by nickel peroxide and some properties of derived polyvinyl alcohol, J. Macromol. Chem. 1, 553–562(1966).Google Scholar
  84. 84.
    T. Nakata, T. Otsu, and M. Imoto, Vinyl polymerization. CLII. The polymerization of vinyl chloride initiated by nickel peroxide, J. Macromol. Chem. 1, 563–579 (1966).Google Scholar
  85. 85.
    T. Nakata, T. Otsu, M. Yamaguchi, and M. Imoto, Vinyl polymerization. CLXXII. Polymerization of methyl methacrylate initiated by nickel peroxide, J. Macromol. Sci. Chem. 1, 1447–1455 (1967).CrossRefGoogle Scholar
  86. 86.
    T. Otsu, M. Yamaguchi, T. Nakata, K. Murata, and M. Ito, Vinyl polymerization. CLXXIII. Effects of water and some reducing agents on the polymerization of vinyl monomers initiated by nickel peroxide, J. Macromol. Soc. Chem. 1, 1457–1468 (1966).CrossRefGoogle Scholar
  87. 87.
    K. Komatsu, S. Nishiyama, J. Hirota, and H. Yasunaga, Polymerization of butadiene. I. Polymerization of butadiene with aluminium halides and metal oxides or peroxides, Kogyo Kagaku Zasshi 72. 2624–2629 (1969); Chem. Abstr. 72, 122585b (1970).Google Scholar
  88. 88.
    K. Komatsu, I. Hirota, Y. Ninomiya, and H. Yasunaga. Polymerization of butadiene. 2. Polymerization of butadiene with aluminium halides and metal oxides or peroxides, Kogyo Kagaku Zasshi 72. 2630–2634 (1969): Chem. Abstr. 72, 122586e (1970).Google Scholar
  89. 89.
    E. Nakatani. Imaging by laser irradiation of semiconductive metal oxides. Japan Kokai, 7482.340 (1974); Chem. Abstr. 82, 78784w (1975).Google Scholar
  90. 90.
    M. Hajek, and J. Malek. Free-radical addition reactions initiated by metal oxides. Paper 5. Metal oxide-initiated alkylation of compounds containing activated methene groups with terminal alkenes, Synthesis 1977, 454–457.Google Scholar
  91. 91.
    M. Tatsuta. Electrolytic preparation of nickel oxide, Japan Kokai 7366,599 (1973); Chem. Abstr. 80, 662131 (1974).Google Scholar
  92. 92.
    J. D. Surmatis, Nickel peroxide oxidizing agent, German Often. 2,415,928 (1974); Chem. Abstr. 82, 75041 r (1975).Google Scholar
  93. J. D. Surmatis, Nickel peroxide oxidizing agent. U.S. Patent No. 4,005,031, (25 January 1977); Chem. Abstr. 86, 140297c (1977).Google Scholar
  94. R. Marbet, Regeneration of nickel peroxide, German OiTen. 2,529,605 (1976); Chem. Abstr. 85, 177685h (1976).Google Scholar
  95. 93.
    H. Ogura, S. Mineo, K. Nakagawa, and S. Shiba, Studies on heterocyclic compounds. XXXIII. Synthesis of [1,2,3]-triazolo [l,5-a]pyridines with nickel peroxide, Yakugaku Zasshi 101, 329–335 (1981); Chem. Abstr. 95, 80801m (1981).Google Scholar
  96. 94.
    J. Sugita, Reaction of chlorophenols with nickel peroxide, Nippon Kagaku Zasshi 87, 741–744 (1966); Chem. Abstr. 65, 15262 (1966).CrossRefGoogle Scholar
  97. 95.
    H. Finkbeiner and A. T. Toothaker, The formation of j-benzoquinones in the oxidation of polyphenylene ethers, J. Org. Chem. 33. 4347–4351 (1968).CrossRefGoogle Scholar
  98. 96.
    A. Ohsawa. H. Arai, H. Ohuishi, and H. Igeta, 1.2.3-Triazinc. J. Chem. Soc. Chem. Commun. 1981, 1174.Google Scholar
  99. 97.
    C. W. Rees and R. C. Storr, Reactive intermediates. Part V. The generation and reactions of 1,8-dehydronaphthalene, J. Chem. Soc. (C) 1969, 760–764.Google Scholar

Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • M. V. George
    • 1
    • 2
  1. 1.Department of ChemistryIndian Institute of Technology KanpurKanpurIndia
  2. 2.Radiation Laboratory and Department of ChemistryUniversity of Notre DameNotre DameUSA

Personalised recommendations