Ruthenium(VIII) Oxide

  1. Martín, Victor S. 1
  2. Palazón, José M. 1
  3. Rodríguez, Carmen M. 1
  4. Nevill, C. Richard
  5. Hutchinson, Douglas K.
  1. 1 Universidad de La Laguna
    info

    Universidad de La Laguna

    San Cristobal de La Laguna, España

    ROR https://ror.org/01r9z8p25

Libro:
Encyclopedia of Reagents for Organic Synthesis

Año de publicación: 2013

Tipo: Entrada de Diccionario

DOI: 10.1002/047084289X.RR009.PUB3 GOOGLE SCHOLAR lock_openAcceso abierto editor

Resumen

image[20427-56-9] O4Ru (MW 165.07)InChI = 1S/4O.RuInChIKey = GJFMDWMEOCWXGJ-UHFFFAOYSA-N(strong oxidant for many functional groups; can cleave double bonds, aromatic rings, and diols1)Alternate Name: ruthenium tetroxide.Physical Data: yellow form: mp 25.5 °C; bp 40 °C; d 3.29 g cm−3. Brownish orange form: mp 27 °C; bp 108 °C (dec).Solubility: slightly sol water; highly sol CHCl3, CCl4.Form Supplied in: although the reagent is commercially available either in solid form or stabilized aqueous solution, it is usually prepared in situ from black solid RuO2 (mw 133.07) [120236-10-1;·xH2O, 32740-79-7] or dark brown (or black) RuCl3 (mw 207.42) [10049-08-8;·xH2O, 14898-67-0], in stoichiometric or catalytic amounts, and an oxidation agent; both of the above Ru salts are widely available.Handling, Storage, and Precautions: handle in a fume hood only. Inhalation should be avoided; vapors irritating to eyes and respiratory tracts, since it readily oxidizes tissue, leaving a deposit of ruthenium dioxide.2 It attacks rubber and reacts explosively with paper filter and alcohol, and violently with ether, benzene, and pyridine.3 However, the use of the catalytic system greatly minimizes the risk in its manipulation, and its usage is strongly recommended.

Referencias bibliográficas

  • Lee, (1973), Oxidation in Organic Chemistry
  • Gore, (1983), Platinum Met. Rev., 27, pp. 111
  • Remy, (1956), Treatise on Inorganic Chemistry, 2, pp. 324
  • Djerassi, (1953), J. Am. Chem. Soc., 75, pp. 3838, 10.1021/ja01111a507
  • Nakata, (1963), Tetrahedron, 19, pp. 1959, 10.1016/0040-4020(63)85009-7
  • Wolfe, (1970), J. Chem. Soc., Chem. Commun., pp. 1420, 10.1039/c29700001420
  • Gopal, (1971), Tetrahedron Lett., pp. 2941, 10.1016/S0040-4039(01)97031-5
  • Berkowitz, (1958), J. Am. Chem. Soc., 80, pp. 6682, 10.1021/ja01557a053
  • Yamamoto, (1985), Tetrahedron Lett., 26, pp. 2107, 10.1016/S0040-4039(00)94791-9
  • Guizard, (1979), J. Fluorine Chem., 13, pp. 175, 10.1016/S0022-1139(00)81086-6
  • Carlsen, (1981), J. Org. Chem., 46, pp. 3936, 10.1021/jo00332a045
  • Matsumoto, (1984), J. Org. Chem., 49, pp. 3435, 10.1021/jo00192a054
  • Kaneda, (1990), J. Chem. Soc., Chem. Commun., pp. 1467, 10.1039/C39900001467
  • Giddings, (1988), J. Org. Chem., 53, pp. 1103, 10.1021/jo00240a037
  • Torii, (1986), J. Org. Chem., 51, pp. 155, 10.1021/jo00352a006
  • Schröder, (1979), J. Chem. Soc., Chem. Commun., 58
  • Paquette, (1987), Tetrahedron Lett., 28, pp. 4965, 10.1016/S0040-4039(00)96671-1
  • Varma, (1992), Tetrahedron Lett., 33, pp. 7719, 10.1016/0040-4039(93)88026-F
  • Seddon, (1984), The Chemistry of Ruthenium, pp. 58
  • Morris, (1990), J. Carbohydr. Chem., 9, pp. 661, 10.1080/07328309008543861
  • Beynon, (1968), Carbohydr. Res., 6, pp. 431, 10.1016/S0008-6215(00)81238-0
  • Parikh, (1965), Can. J. Chem., 43, pp. 3452, 10.1139/v65-483
  • Dehand, (1979), J. Chem. Res. (S), pp. 155
  • Hamon, (1993), Tetrahedron: Asymmetry, 4, pp. 1435, 10.1016/S0957-4166(00)80334-1
  • Kasai, (1983), J. Org. Chem., 48, pp. 712, 10.1021/jo00153a018
  • Niwa, (1991), Tetrahedron Lett., 32, pp. 1329, 10.1016/S0040-4039(00)79659-6
  • Singh, (1992), Tetrahedron Lett., 33, pp. 2307, 10.1016/S0040-4039(00)74197-9
  • Müller, (1981), Tetrahedron Lett., 22, pp. 2361, 10.1016/S0040-4039(01)82906-3
  • Bilgrien, (1987), J. Am. Chem. Soc., 109, pp. 3786, 10.1021/ja00246a049
  • Genet, (1989), Synth. Commun., 19, pp. 1721, 10.1080/00397918908051071
  • Griffith, (1987), Chem. Commun./J. Chem. Soc., pp. 1625, 10.1039/c39870001625
  • Meyers, (1987), J. Org. Chem., 52, pp. 4592, 10.1021/jo00229a028
  • Behr, (1991), J. Organomet. Chem., 403, pp. 209, 10.1016/0022-328X(91)83101-9
  • Hudlický, (1990), Oxidations in Organic Chemistry
  • Larock, (1989), Comprehensive Organic Transformations
  • Comprehensive Organic Synthesis 1991 7
  • Moriarty, (1970), Tetrahedron Lett., pp. 4003, 10.1016/S0040-4039(01)98650-2
  • Nutt, (1965), J. Am. Chem. Soc., 87, pp. 3273, 10.1021/ja01092a064
  • Nutt, (1968), J. Org. Chem., 33, pp. 1789, 10.1021/jo01269a019
  • Beynon, (1964), Proc. Chem. Soc. London, pp. 342
  • Caputo, (1967), Tetrahedron Lett., pp. 4729, 10.1016/S0040-4039(01)89591-5
  • Gopal, (1972), Tetrahedron, 28, pp. 4259, 10.1016/S0040-4020(01)88948-1
  • Crawford, (1983), J. Org. Chem., 48, pp. 1366, 10.1021/jo00156a048
  • Askin, (1987), J. Org. Chem., 52, pp. 622, 10.1021/jo00380a025
  • Hernández, (1992), Synthesis, pp. 653, 10.1055/s-1992-26190
  • Rodríguez, (1992), Tetrahedron, 48, pp. 3571, 10.1016/S0040-4020(01)88494-5
  • Gao, (1988), J. Am. Chem. Soc., 110, pp. 7538, 10.1021/ja00230a045
  • Ikunaka, (1987), Agric. Biol. Chem., 51, pp. 565, 10.1271/bbb1961.51.565
  • Schuda, (1983), Tetrahedron Lett., 24, pp. 3829, 10.1016/S0040-4039(00)94286-2
  • Takeda, (1987), J. Am. Chem. Soc., 109, pp. 914, 10.1021/ja00237a055
  • Morris, (1987), J. Org. Chem., 52, pp. 1149, 10.1021/jo00382a035
  • Dauben, (1983), J. Org. Chem., 48, pp. 2842, 10.1021/jo00165a012
  • Mori, (1987), Tetrahedron, 43, pp. 2229, 10.1016/S0040-4020(01)86806-X
  • Smith, (1980), Synth. Commun., 10, pp. 205, 10.1080/00397918008064223
  • Tang, (1978), J. Chem. Soc., Chem. Commun., pp. 562, 10.1039/c39780000562
  • Sheehan, (1974), J. Org. Chem., 39, pp. 2264, 10.1021/jo00929a030
  • Tanaka, (1988), Chem. Pharm. Bull., 36, pp. 3125, 10.1248/cpb.36.3125
  • Yoshifuji, (1985), Chem. Pharm. Bull., 33, pp. 1749, 10.1248/cpb.33.1749
  • Balavoine, (1984), Tetrahedron Lett., 25, pp. 3187, 10.1016/S0040-4039(01)91004-4
  • Kametani, (1985), Chem. Lett., pp. 485, 10.1246/cl.1985.485
  • Carling, (1992), J. Chem. Soc., Perkin Trans. 1, pp. 95, 10.1039/p19920000095
  • Tenaglia, (1989), Tetrahedron Lett., 30, pp. 5271, 10.1016/S0040-4039(01)93761-X
  • Tenaglia, (1989), Tetrahedron Lett., 30, pp. 5275, 10.1016/S0040-4039(01)93762-1
  • Clinch, (1987), Tetrahedron Lett., 28, pp. 6425, 10.1016/S0040-4039(00)96878-3
  • Mori, (1986), Tetrahedron, 42, pp. 4413, 10.1016/S0040-4020(01)87280-X
  • Mehta, (1986), J. Chem. Soc., Chem. Commun., pp. 1319, 10.1039/c39860001319
  • Schröder, (1980), Chem. Rev., 80, pp. 187, 10.1021/cr60324a003
  • Piatak, (1969), J. Org. Chem., 34, pp. 112, 10.1021/jo00838a027
  • Webster, (1987), J. Org. Chem., 52, pp. 689, 10.1021/jo00380a040
  • Hartmann, (1993), Tetrahedron Lett., 34, pp. 1487, 10.1016/S0040-4039(00)60325-8
  • Deprés, (1985), J. Org. Chem., 50, pp. 1972, 10.1021/jo00211a036
  • Spitzer, (1974), J. Org. Chem., 39, pp. 2468, 10.1021/jo00930a051
  • Nuñez, (1990), J. Org. Chem., 55, pp. 1928, 10.1021/jo00293a044
  • Kusakabe, (1989), J. Org. Chem., 54, pp. 2085, 10.1021/jo00270a015
  • Danishefsky, (1985), J. Am. Chem. Soc., 107, pp. 7762, 10.1021/ja00311a090
  • Danishefsky, (1988), J. Am. Chem. Soc., 110, pp. 3929, 10.1021/ja00220a035
  • Brown, (1991), Tetrahedron Lett., 32, pp. 5187, 10.1016/S0040-4039(00)93462-2
  • Kasai, (1983), J. Org. Chem., 48, pp. 2346, 10.1021/jo00162a009
  • Ayres, (1975), J. Chem. Soc., Perkin Trans. 1, pp. 707, 10.1039/p19750000707
  • Martín, (1988), Tetrahedron Lett., 29, pp. 2701, 10.1016/0040-4039(88)85264-X
  • Martres, (1993), Tetrahedron Lett., 34, pp. 629, 10.1016/S0040-4039(00)61637-4
  • Tenaglia, (1992), J. Org. Chem., 57, pp. 5523, 10.1021/jo00046a040
  • Mueller, (1975), J. Chem. Soc., Chem. Commun., pp. 565, 10.1039/c39750000565
  • Johnston, (1985), J. Org. Chem., 50, pp. 114, 10.1021/jo00201a022
  • Lee, (1984), Can. J. Chem., 62, pp. 1835, 10.1139/v84-314
  • Coates, (1982), J. Org. Chem., 47, pp. 3597, 10.1021/jo00140a001
  • Corey, (1978), J. Am. Chem. Soc., 100, pp. 8034, 10.1021/ja00493a056
  • Varma, (1992), Tetrahedron Lett., 33, pp. 7719, 10.1016/0040-4039(93)88026-F
  • Green, (1984), J. Chem. Soc., Perkin Trans. 1, pp. 681, 10.1039/P19840000681
  • Bailey, (1993), lnorg. Chem., 32, pp. 268, 10.1021/ic00055a006
  • Guertin, (1993), Tetrahedron Lett., 34, pp. 5369, 10.1016/S0040-4039(00)73911-6
  • Ohtake, (1992), Tetrahedron Lett., 33, pp. 2521, 10.1016/S0040-4039(00)92231-7
  • Tomioka, (1981), Tetrahedron Lett., 22, pp. 1605, 10.1016/S0040-4039(01)90389-2
  • Murahashi, (1993), Tetrahedron Lett., 34, pp. 1299, 10.1016/S0040-4039(00)91779-9
  • Matsumoto, (1981), Chem. Commun./J. Chem. Soc., pp. 907, 10.1039/c39810000907
  • Kanemoto, (1983), Tetrahedron Lett., 24, pp. 2185, 10.1016/S0040-4039(00)81878-X
  • Sharpless, (1976), Tetrahedron Lett., pp. 2503, 10.1016/S0040-4039(00)78130-5
  • Tanaka, (1984), Angew. Chem., Int. Ed. Engl., 23, pp. 518, 10.1002/anie.198405181
  • Sasson, (1971), Tetrahedron Lett., pp. 2167, 10.1016/S0040-4039(01)96811-X
  • Regen, (1972), J. Org. Chem., 37, pp. 1832, 10.1021/jo00976a038
  • Müller, (1981), Helv. Chim. Acta, 64, pp. 2531, 10.1002/hlca.19810640807
  • Ishii, (1986), J. Org. Chem., 51, pp. 2034, 10.1021/jo00361a018
  • Murahashi, (1987), J. Org. Chem., 52, pp. 4319, 10.1021/jo00228a032
  • Murahashi, (1992), Tetrahedron Lett., 33, pp. 6991, 10.1016/S0040-4039(00)60914-0
  • Murahashi, (1991), Tetrahedron Lett., 32, pp. 5991, 10.1016/S0040-4039(00)79446-9
  • Griffith, (1990), J. Chem. Soc., Chem. Commun., pp. 1219, 10.1039/c39900001219
  • Murahashi, (2000), Biomimetic Oxidation Catalyzed by Transition Metal Complexes, pp. 563, 10.1142/9781848160699_0013
  • Naota, (1998), Chem. Rev., 98, pp. 2599, 10.1021/cr9403695
  • Bas, (2001), Synthesis, pp. 2495, 10.1055/s-2001-18720
  • Dondoni, (1994), Synthesis, pp. 1450, 10.1055/s-1994-25712
  • Giovannini, (1997), Tetrahedron Lett., 38, pp. 3781, 10.1016/S0040-4039(97)00734-X
  • Crich, (1999), Synth. Commun., 29, pp. 359, 10.1080/00397919908085778
  • Yang, (2004), J. Org. Chem., 69, pp. 2221, 10.1021/jo0357925
  • Cornely, (2003), Green Chemistry, 5, pp. 34, 10.1039/b210880c
  • Miranda, (2004), Synthesis, pp. 1767
  • Lai, (2002), lnorg. Chem., 41, pp. 1954, 10.1021/ic0108336
  • Lee, (1995), Can. J. Chem., 73, pp. 49, 10.1139/v95-007
  • Frunzke, (2004), J. Am. Chem. Soc., 126, pp. 3642, 10.1021/ja039921a
  • Shing, (1994), Angew. Chem., Int. Ed. Engl., 33, pp. 2312, 10.1002/anie.199423121
  • Plietker, (2004), Org. Biomol. Chem., 2, pp. 1116, 10.1039/b316546a
  • Plietker, (2003), OL, 5, pp. 3353, 10.1021/ol035335a
  • Couturier, (2002), OPRD, 6, pp. 42, 10.1021/op0102161
  • Meier, (2001), Org. Lett., 3, pp. 1717, 10.1021/ol0159120
  • Murahashi, (1993), J. Org. Chem., 58, pp. 2929, 10.1021/jo00063a002
  • Plietker, (2003), J. Org. Chem., 68, pp. 7123, 10.1021/jo034864p
  • Plietker, (2004), Org. Biomol. Chem., 2, pp. 2403, 10.1039/B407937J
  • Kirsch, (2000), Eur. J. Org. Chem., pp. 1741, 10.1002/(SICI)1099-0690(200005)2000:9<1741::AID-EJOC1741>3.0.CO;2-W
  • Plietker, (2004), OL, 6, pp. 289, 10.1021/ol0362663
  • Behr, (2004), Eur. J. Org. Chem., pp. 3884, 10.1002/ejoc.200400219
  • Piccialli, (2000), Tetrahedron Lett., 41, pp. 3731, 10.1016/S0040-4039(00)00476-7
  • Albarella, (2001), Eur. J. Org. Chem., pp. 997, 10.1002/1099-0690(200103)2001:5<997::AID-EJOC997>3.0.CO;2-7
  • Nevill, (1998), Tetrahedron Lett., 39, pp. 5671, 10.1016/S0040-4039(98)01142-3
  • Yoshifuji, (1987), Chem. Pharm. Bull., 35, pp. 2994, 10.1248/cpb.35.2994
  • Ranganathan, (1998), J. Indian Chem. Soc., 75, pp. 583
  • Bakke, (1996), J. Phys. Org. Chem., 9, pp. 310, 10.1002/(SICI)1099-1395(199606)9:6<310::AID-POC790>3.0.CO;2-E
  • Bakke, (1995), Acta Chem. Scand., 49, pp. 615, 10.3891/acta.chem.scand.49-0615
  • Bakke, (1996), J. Phys. Org. Chem., 9, pp. 507, 10.1002/(SICI)1099-1395(199607)9:7<507::AID-POC811>3.0.CO;2-L
  • Bakke, (1994), Acta Chem. Scand., 48, pp. 160, 10.3891/acta.chem.scand.48-0160
  • Coudret, (1996), Tetrahedron Lett., 37, pp. 2425, 10.1016/0040-4039(96)00325-5
  • Hasegawa, (1985), Chem. Lett., pp. 1385, 10.1246/cl.1985.1385
  • Kawai, (2003), Chem. Pharm. Bull., 51, pp. 291, 10.1248/cpb.51.291
  • Arakawa, (2003), Chem. Pharm. Bull., 51, pp. 1015, 10.1248/cpb.51.1015
  • Griffith, (2003), Synth. Commun., 33, pp. 2945, 10.1081/SCC-120022466
  • Yang, (2001), J. Org. Chem., 66, pp. 4814, 10.1021/jo010122p
  • Sharma, (2004), J. Org. Chem., 69, pp. 5742, 10.1021/jo0491861
  • Kraft, (2003), Eur. J. Org. Chem., pp. 3735, 10.1002/ejoc.200300174
  • Tochtermann, (1993), Chem. Ber., 126, pp. 2547, 10.1002/cber.19931261133
  • Ferraz, (2003), Org. Lett., 5, pp. 1337, 10.1021/ol0342958
  • Piccialli, (2001), Tetrahedron Lett, 42, pp. 4695, 10.1016/S0040-4039(01)00790-0
  • Bifulco, (2002), Tetrahedron Lett, 43, pp. 9265, 10.1016/S0040-4039(02)02304-3
  • Bifulco, (2003), Tetrahedron Lett, 44
  • Albarella, (2001), Eur. J. Org. Chem, pp. 997, 10.1002/1099-0690(200103)2001:5<997::AID-EJOC997>3.0.CO;2-7
  • Roth, (2005), Eur. J. Org. Chem, pp. 4109, 10.1002/ejoc.200500052
  • Zhong, (1997), J. Org. Chem, 62, pp. 2622, 10.1021/jo9621581
  • Göksel, (2006), Org. Lett, 8, pp. 3433, 10.1021/ol060520k
  • Gühler, (2007), Org. Biomol. Chem, 5, pp. 1605, 10.1039/B702877F
  • Piccialli, (2008), Tetrahedron, 65, pp. 11185, 10.1016/j.tet.2008.09.052
  • Plietker, (2005), Synthesis, pp. 2453, 10.1055/s-2005-872172