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Volumn , Issue 10, 1996, Pages 1153-1174

On the use of stable organic nitroxyl radicals for the oxidation of primary and secondary alcohols

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EID: 0029829555     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review
Times cited : (669)

References (148)
  • 1
    • 0001174130 scopus 로고
    • Wiley: New York
    • Fieser, L.F.; Fieser, M. In Reagents for Organic Synthesis; Vol. 1; Wiley: New York, 1967, pp 142-147, 1059-1064. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington DC, 1990.
    • (1967) Reagents for Organic Synthesis , vol.1 , pp. 142-147
    • Fieser, L.F.1    Fieser, M.2
  • 2
    • 0003678023 scopus 로고
    • ACS Monograph 186; American Chemical Society: Washington DC
    • Fieser, L.F.; Fieser, M. In Reagents for Organic Synthesis; Vol. 1; Wiley: New York, 1967, pp 142-147, 1059-1064. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington DC, 1990.
    • (1990) Oxidations in Organic Chemistry
    • Hudlicky, M.1
  • 3
    • 0000206354 scopus 로고
    • Poos, G.I.; Arth, G.E.; Beyler, R.E.; Sarett, L.H. J. Am. Chem. Soc. 1953, 75, 422. Collins, J.C.; Hess, W.W.; Frank, F.J. Tetrahedron Lett. 1968, 3363. Ratcliffe, R.; Rodehorst, R. J. Org. Chem. 1970, 35, 4000.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 422
    • Poos, G.I.1    Arth, G.E.2    Beyler, R.E.3    Sarett, L.H.4
  • 4
    • 49949122286 scopus 로고
    • Poos, G.I.; Arth, G.E.; Beyler, R.E.; Sarett, L.H. J. Am. Chem. Soc. 1953, 75, 422. Collins, J.C.; Hess, W.W.; Frank, F.J. Tetrahedron Lett. 1968, 3363. Ratcliffe, R.; Rodehorst, R. J. Org. Chem. 1970, 35, 4000.
    • (1968) Tetrahedron Lett. , pp. 3363
    • Collins, J.C.1    Hess, W.W.2    Frank, F.J.3
  • 5
    • 33947297262 scopus 로고
    • Poos, G.I.; Arth, G.E.; Beyler, R.E.; Sarett, L.H. J. Am. Chem. Soc. 1953, 75, 422. Collins, J.C.; Hess, W.W.; Frank, F.J. Tetrahedron Lett. 1968, 3363. Ratcliffe, R.; Rodehorst, R. J. Org. Chem. 1970, 35, 4000.
    • (1970) J. Org. Chem. , vol.35 , pp. 4000
    • Ratcliffe, R.1    Rodehorst, R.2
  • 6
    • 49549138922 scopus 로고
    • Corey, E.J.; Suggs, J.W. Tetrahedron Lett. 1975, 2647. For a review, see: Piancatelli, G.; Scettri, A.; D'Auria, M. Synthesis 1982, 245.
    • (1975) Tetrahedron Lett. , pp. 2647
    • Corey, E.J.1    Suggs, J.W.2
  • 8
    • 0001666755 scopus 로고
    • Coates, W.M.; Corrigan, J.R. Chem. Ind. 1969, 44, 1594. Corey, E.J.; Schmidt, G. Tetrahedron Lett. 1979, 399.
    • (1969) Chem. Ind. , vol.44 , pp. 1594
    • Coates, W.M.1    Corrigan, J.R.2
  • 10
    • 84989478646 scopus 로고
    • For reviews, see: Mancuso, A.J.; Swern, D. Synthesis 1981, 165. Tidwell, T.T. Synthesis 1990, 857.
    • (1981) Synthesis , pp. 165
    • Mancuso, A.J.1    Swern, D.2
  • 11
    • 85082551132 scopus 로고
    • For reviews, see: Mancuso, A.J.; Swern, D. Synthesis 1981, 165. Tidwell, T.T. Synthesis 1990, 857.
    • (1990) Synthesis , pp. 857
    • Tidwell, T.T.1
  • 12
    • 33644528891 scopus 로고
    • Dess, D.B.; Martin, J.C. J. Org. Chem. 1983, 48, 4155. Dess, D.B.; Martin, J.C. J. Am. Chem. Soc. 1991, 113, 7277.
    • (1983) J. Org. Chem. , vol.48 , pp. 4155
    • Dess, D.B.1    Martin, J.C.2
  • 15
  • 16
    • 0004193472 scopus 로고
    • Plenum Press: New York-London, Translated from Russian
    • Rozantsev, E.G. Free Nitroxyl Radicals; Plenum Press: New York-London, 1970 (Translated from Russian.) Rozantsev, E.G.; Sholle, V.D. Synthesis 1971, 190. Rozantsev, E.G.; Sholle, V.D. Synthesis 1971, 401.
    • (1970) Free Nitroxyl Radicals
    • Rozantsev, E.G.1
  • 17
    • 84989752057 scopus 로고
    • Rozantsev, E.G. Free Nitroxyl Radicals; Plenum Press: New York-London, 1970 (Translated from Russian.) Rozantsev, E.G.; Sholle, V.D. Synthesis 1971, 190. Rozantsev, E.G.; Sholle, V.D. Synthesis 1971, 401.
    • (1971) Synthesis , pp. 190
    • Rozantsev, E.G.1    Sholle, V.D.2
  • 18
    • 85012596673 scopus 로고
    • Rozantsev, E.G. Free Nitroxyl Radicals; Plenum Press: New York-London, 1970 (Translated from Russian.) Rozantsev, E.G.; Sholle, V.D. Synthesis 1971, 190. Rozantsev, E.G.; Sholle, V.D. Synthesis 1971, 401.
    • (1971) Synthesis , pp. 401
    • Rozantsev, E.G.1    Sholle, V.D.2
  • 22
    • 0011634086 scopus 로고
    • Golubev, V.A.; Rozantsev, E.G.; Neiman, M.B. Izv. Akad. Nauk SSSR, Ser. Khim. 1965, 1927; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1965, 1898.
    • (1965) Bull. Acad. Sci. USSR, Div. Chem. Sci. , pp. 1898
  • 32
    • 84945094507 scopus 로고
    • The first conjugated organic nitroxyl, porphyrexide, was prepared in 1901: Piloty, O.; Graf Schwerin, B. Ber. Dtsch. Chem. Ges. 1901, 34, 1870. Piloty, O.; Graf Schwerin, B. Ber. Dtsch. Chem. Ges. 1901, 34, 2354.
    • (1901) Ber. Dtsch. Chem. Ges. , vol.34 , pp. 1870
    • Piloty, O.1    Graf Schwerin, B.2
  • 33
    • 84981760138 scopus 로고
    • The first conjugated organic nitroxyl, porphyrexide, was prepared in 1901: Piloty, O.; Graf Schwerin, B. Ber. Dtsch. Chem. Ges. 1901, 34, 1870. Piloty, O.; Graf Schwerin, B. Ber. Dtsch. Chem. Ges. 1901, 34, 2354.
    • (1901) Ber. Dtsch. Chem. Ges. , vol.34 , pp. 2354
    • Piloty, O.1    Graf Schwerin, B.2
  • 36
    • 33646111612 scopus 로고
    • Lebedev, O.L.; Kazarnovskii, S.N. Zhur. Obshch. Khim. 1960, 30, 1631; Chem. Abstr. 1961, 55, 1473a.
    • (1961) Chem. Abstr. , vol.55
  • 42
    • 33748407078 scopus 로고
    • Perkins, M. J. Adv. Phys. Org. Chem. 1980, 17, 1. Beckwith, A.L.J.; Bowry, V.W.; Ingold, K.U. J. Am. Chem. Soc. 1992, 114, 4983. Bowry, V.W.; Ingold, K.U. J. Am. Chem. Soc. 1992, 114, 4992.
    • (1980) J. Adv. Phys. Org. Chem. , vol.17 , pp. 1
    • Perkins, M.1
  • 43
    • 0000745524 scopus 로고
    • Perkins, M. J. Adv. Phys. Org. Chem. 1980, 17, 1. Beckwith, A.L.J.; Bowry, V.W.; Ingold, K.U. J. Am. Chem. Soc. 1992, 114, 4983. Bowry, V.W.; Ingold, K.U. J. Am. Chem. Soc. 1992, 114, 4992.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4983
    • Beckwith, A.L.J.1    Bowry, V.W.2    Ingold, K.U.3
  • 44
    • 0000745523 scopus 로고
    • Perkins, M. J. Adv. Phys. Org. Chem. 1980, 17, 1. Beckwith, A.L.J.; Bowry, V.W.; Ingold, K.U. J. Am. Chem. Soc. 1992, 114, 4983. Bowry, V.W.; Ingold, K.U. J. Am. Chem. Soc. 1992, 114, 4992.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4992
    • Bowry, V.W.1    Ingold, K.U.2
  • 45
    • 10244227201 scopus 로고    scopus 로고
    • Numerous references to the work of these groups can be found under reference 8 and 26
    • Numerous references to the work of these groups can be found under reference 8 and 26.
  • 53
    • 0000177515 scopus 로고
    • Sümmermann, W.; Deffner, U. Tetrahedron 1975, 31, 593. Shchukin, G.I.; Ryabinin, V.A.; Grigor'ev, I.A.; Volodarskii, L.B. Zhur. Obshch. Khim. 1986, 56, 855; Chem. Abstr. 1986, 105, 190330.
    • (1975) Tetrahedron , vol.31 , pp. 593
    • Sümmermann, W.1    Deffner, U.2
  • 55
    • 10244230167 scopus 로고
    • Sümmermann, W.; Deffner, U. Tetrahedron 1975, 31, 593. Shchukin, G.I.; Ryabinin, V.A.; Grigor'ev, I.A.; Volodarskii, L.B. Zhur. Obshch. Khim. 1986, 56, 855; Chem. Abstr. 1986, 105, 190330.
    • (1986) Chem. Abstr. , vol.105 , pp. 190330
  • 56
    • 84982351241 scopus 로고
    • Examples of oxidations with nitroxyl radicals without interference of the oxoammonium salt: Brackman, W.; Gaasbeek, C.J. Rec. Trav. Chim. 1966, 85, 221. Mendenhall, G.D.; Ingold, K.U. J. Am. Chem. Soc. 1973, 95, 6395. Chan, T.W.; Bruice, T.C. J. Am. Chem. Soc. 1977, 99, 7287.
    • (1966) Rec. Trav. Chim. , vol.85 , pp. 221
    • Brackman, W.1    Gaasbeek, C.J.2
  • 57
    • 0003629378 scopus 로고
    • Examples of oxidations with nitroxyl radicals without interference of the oxoammonium salt: Brackman, W.; Gaasbeek, C.J. Rec. Trav. Chim. 1966, 85, 221. Mendenhall, G.D.; Ingold, K.U. J. Am. Chem. Soc. 1973, 95, 6395. Chan, T.W.; Bruice, T.C. J. Am. Chem. Soc. 1977, 99, 7287.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 6395
    • Mendenhall, G.D.1    Ingold, K.U.2
  • 58
    • 0017784010 scopus 로고
    • Examples of oxidations with nitroxyl radicals without interference of the oxoammonium salt: Brackman, W.; Gaasbeek, C.J. Rec. Trav. Chim. 1966, 85, 221. Mendenhall, G.D.; Ingold, K.U. J. Am. Chem. Soc. 1973, 95, 6395. Chan, T.W.; Bruice, T.C. J. Am. Chem. Soc. 1977, 99, 7287.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 7287
    • Chan, T.W.1    Bruice, T.C.2
  • 60
  • 63
    • 10244263988 scopus 로고    scopus 로고
    • note
    • The first two examples of reference 37 are the only reports we are aware of in which a primary or a secondary alcohol is oxidised uing nitroxyl radical without interference of an oxoammonium salt.
  • 65
    • 10244260867 scopus 로고
    • Golubev, V.A.; Voronina, G.N. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 2089; Bull. Acad. Sci. USSR, Div. Chim. Sci. 1972, 2024.
    • (1972) Bull. Acad. Sci. USSR, Div. Chim. Sci. , pp. 2024
  • 67
  • 69
    • 0001977737 scopus 로고
    • Golubev, V.A.; Sen', V.D.; Kulyk, I.V.; Aleksandrov, A.L. Izv. Akad. Nauk SSSR, Ser. Khim. 1975, 2235; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1975, 2119.
    • (1975) Bull. Acad. Sci. USSR, Div. Chem. Sci. , pp. 2119
  • 75
    • 0003491536 scopus 로고
    • Golubev, V.A.; Borislavskii, V.N.; Aleksandrov, A.L. Izv. Akad. Nauk SSSR, Ser. Khim. 1977, 2025; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1977, 1874.
    • (1977) Bull. Acad. Sci. USSR, Div. Chem. Sci. , pp. 1874
  • 86
    • 0344327467 scopus 로고
    • Friess, S.L. J. Am. Chem. Soc. 1949, 71, 2571. Friess, S.L.; Frankenburg, P.E. J. Am. Chem. Soc. 1952, 74, 2679.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 2571
    • Friess, S.L.1
  • 121
    • 10244233364 scopus 로고
    • Ogibin, Yu. N.; Khusid, A.Kh.; Nikishin, G.I. Izv. Akad. Nauk, Ser. Khim. 1992, 941; Bull. Acad. Sci, Russia, Div. Chem. Sci. 1992, 735.
    • (1992) Bull. Acad. Sci, Russia, Div. Chem. Sci. , pp. 735
  • 126
    • 10244279659 scopus 로고
    • Ph.D. Thesis, University of Leiden
    • van Boom, S.S.G.E. Ph.D. Thesis, University of Leiden, 1995.
    • (1995)
    • Van Boom, S.S.G.E.1
  • 135
    • 10244227200 scopus 로고    scopus 로고
    • German Patent 3 705 785, 1988
    • Knaus, G.H.; Paust, J. German Patent 3 705 785, 1988; Chem. Abstr. 1989, 110, 75844.
    • Knaus, G.H.1    Paust, J.2
  • 136
    • 10244248219 scopus 로고
    • Knaus, G.H.; Paust, J. German Patent 3 705 785, 1988; Chem. Abstr. 1989, 110, 75844.
    • (1989) Chem. Abstr. , vol.110 , pp. 75844
  • 137
    • 10244233363 scopus 로고    scopus 로고
    • German Patent 4 007 923, 1990
    • Kuekenhoehner, T.; Goetz, N. German Patent 4 007 923, 1990; Chem. Abstr. 1991, 114, 163728.
    • Kuekenhoehner, T.1    Goetz, N.2
  • 138
    • 10244266809 scopus 로고
    • Kuekenhoehner, T.; Goetz, N. German Patent 4 007 923, 1990; Chem. Abstr. 1991, 114, 163728.
    • (1991) Chem. Abstr. , vol.114 , pp. 163728
  • 139
    • 10244230166 scopus 로고    scopus 로고
    • U.S. Patents 51 36 103, 1992; 5 136 102, 1992; 5 136 101, 1992; 5 155 280, 1992; 5 155 279, 1992; 5 155 278, 1992; 5162579, 1992; 5166423, 1992; 5166422, 1992; 5 179 218, 1993; 5 175 359, 1992; 5 239 116, 1993; 5 250 727, 1993; Chem. Abstr. (respectively) 1992, 117, 212015; 1992, 117, 212016; 1992, 117, 212017; 1993, 118, 24098; 1993, 118, 41 189; 1993, 118, 41 190; 1993, 118, 41 196; 1993, 118, 83 271; 1993, 118, 83 272; 1993, 118, 212496; 1993, 118, 212 765; 1993, 119, 249 586; 1994, 120, 137 710.
    • Fried, H.E. U.S. Patents 51 36 103, 1992; 5 136 102, 1992; 5 136 101, 1992; 5 155 280, 1992; 5 155 279, 1992; 5 155 278, 1992; 5162579, 1992; 5166423, 1992; 5166422, 1992; 5 179 218, 1993; 5 175 359, 1992; 5 239 116, 1993; 5 250 727, 1993; Chem. Abstr. (respectively) 1992, 117, 212015; 1992, 117, 212016; 1992, 117, 212017; 1993, 118, 24098; 1993, 118, 41 189; 1993, 118, 41 190; 1993, 118, 41 196; 1993, 118, 83 271; 1993, 118, 83 272; 1993, 118, 212496; 1993, 118, 212 765; 1993, 119, 249 586; 1994, 120, 137 710.
    • Fried, H.E.1
  • 141
    • 0345138832 scopus 로고
    • Casciani, R.V.; Likibi, P.J.-M.; McGraw, G.L. German Patent 4209869, 1992; Chem. Abstr. 1993, 119, 9389.
    • (1993) Chem. Abstr. , vol.119 , pp. 9389
  • 143
    • 0003491550 scopus 로고
    • Golubev, V.A.; Zhdanov, R.I.; Protsishin, I.T.; Rozantsev, E.G. Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 2158; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1970, 2043. Golubev, V.A.; Rudyk, T.S.; Sen', V.D.; Aleksandrov, A.L. Izv. Akad. Nauk SSSR. Ser. Khim. 1976, 763; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1976, 744.
    • (1970) Bull. Acad. Sci. USSR, Div. Chem. Sci. , pp. 2043
  • 144
    • 0005733938 scopus 로고
    • Golubev, V.A.; Zhdanov, R.I.; Protsishin, I.T.; Rozantsev, E.G. Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 2158; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1970, 2043. Golubev, V.A.; Rudyk, T.S.; Sen', V.D.; Aleksandrov, A.L. Izv. Akad. Nauk SSSR. Ser. Khim. 1976, 763; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1976, 744.
    • (1976) Izv. Akad. Nauk SSSR. Ser. Khim. , pp. 763
    • Golubev, V.A.1    Rudyk, T.S.2    Sen', V.D.3    Aleksandrov, A.L.4
  • 145
    • 0003491544 scopus 로고
    • Golubev, V.A.; Zhdanov, R.I.; Protsishin, I.T.; Rozantsev, E.G. Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 2158; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1970, 2043. Golubev, V.A.; Rudyk, T.S.; Sen', V.D.; Aleksandrov, A.L. Izv. Akad. Nauk SSSR. Ser. Khim. 1976, 763; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1976, 744.
    • (1976) Bull. Acad. Sci. USSR, Div. Chem. Sci. , pp. 744


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