Skip to main content
SpringerLink
Log in

Oxidation of Alkanes

  • Chapter
  • First Online:
Ruthenium Oxidation Complexes

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 34))

  • 1396 Accesses

Abstract

This chapter covers oxidation of C–H and C–C bonds in alkanes. Section 4.1 concerns oxidation of C–H bonds: aldehydes and other CH species (4.1.1), methylene (–CH2 groups) (4.1.2) and methyl (–CH3) groups (4.1.3). This is followed by the oxidation of cyclic alkanes (4.1.4) and large-scale alkane oxidations (4.1.5). Alkane oxidations not considered here but covered in Chapter 1 are listed in Section 4.1.6. The final section (4.2) concerns oxidative cleavage of C–C bonds.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Che CK, Lau TC (2004) In: Constable EC, Dilworth JR (eds) Comprehensive coordination chemistry II, vol 5. Elsevier Pergamon, Amsterdam, pp 733–847

    Chapter  Google Scholar 

  2. Murahashi SI, Komiya N (2004) In: Bäckvall JE (ed) Modern oxidation methods. Wiley VCH Verlag GmbH, Weinheim, 2004, pp 165–191

    Google Scholar 

  3. Murahashi SI, Komiya N (2004) In: Murahashi SI (ed) Ruthenium in organic synthesis. Wiley-VCH, Weinheim, pp 53–93

    Chapter  Google Scholar 

  4. Komiya S, Hirano M (2004) In: Murahashi SI (ed) Ruthenium in organic synthesis. Wiley-VCH, Weinheim, pp 345–366

    Google Scholar 

  5. Courtney JL (1986) In: Mijs WJ, de Jonge CRHI (eds) Organic syntheses by oxidation with metal compounds. Plenum Press, New York, pp 445–467

    Chapter  Google Scholar 

  6. Haines AH (1985) Methods for the oxidation of organic compounds – alkanes, alkenes, alkynes and arenes. Academic Press, London

    Google Scholar 

  7. Tandon PK, Baboo R, Singh AK Gayatri K (2006) Appl Organomet Chem 20:20–23

    Article  CAS  Google Scholar 

  8. Bailey AJ, Griffith WP, Mostafa SI, Sherwood PA (1993) Inorg Chem 32:268–271

    Article  CAS  Google Scholar 

  9. Green G, Griffith WP, Hollinshead DM, Ley SV, Schröder MJ (1984) Chem Soc Perkin Trans 1:681–686

    Google Scholar 

  10. Rajendran S, Trivedi DC (1995) Synthesis 153–154

    Google Scholar 

  11. Torii S, Inokuchi T, Sugiura TJ (1986) J Org Chem 51:155–166

    Article  CAS  Google Scholar 

  12. Owston NA, Nixon TD, Parker AJ, Whittlesey MK, Williams JMJ (2000) Synthesis 1578–1581

    Google Scholar 

  13. Tanaka M, Kobayashi TA, Sakakura T (1984) Angew Chem Int Edit 23:518–519

    Article  Google Scholar 

  14. Toullec PK, Bonaccorsi C, Mezzetti A, Togni A (2004) Proc Natl Acad Sci USA 101:5010–5014

    Article  CAS  Google Scholar 

  15. Shingaki T, Miura K, Higuchi T, Hirobe M, Nagano T (1997) Chem Commun 861–862

    Google Scholar 

  16. Hasegawa T, Niwa H, Yamada K (1985) Chem Lett 1385–1386

    Google Scholar 

  17. Murahashi SI, Komiya N, Oda Y, Kuwabara T, Naota TJ (2000) J Org Chem 65:9186–9193

    Article  CAS  Google Scholar 

  18. Murahashi SI, Oda Y, Naota T, Kuwabara T (1993) Tetrahedron Lett 34:1299–1302

    Article  CAS  Google Scholar 

  19. El-Hendawy AM, Alqaradawi SY, Al-Madfa HA (2000) Transit Met Chem 25:572–578

    Article  CAS  Google Scholar 

  20. Murahashi SI, Naota T, Kuwabara T (1989) Synlett 1:62–63

    Google Scholar 

  21. Bailey AJ, Griffith WP, Savage PD (1995) J Chem Soc Dalton Trans 3537–3542

    Google Scholar 

  22. Sasson Y, Al Quntar AEA, Zoran A (1998) Chem Commun 73–74

    Google Scholar 

  23. Carrijo RMC, Romero JR (1994) Synthetic Commun 24:433–440

    Article  CAS  Google Scholar 

  24. Barak G, Sasson Y (1988) J Chem Soc Chem Commun 637–638

    Google Scholar 

  25. Spitzer UA, Lee DGJ (1975) J Org Chem 40:2539–2540

    Article  CAS  Google Scholar 

  26. Yamaguchi M, Ichii Y, Kosaka S, Masui D, Yamagishi T (2002) Chem Lett 434–435

    Google Scholar 

  27. Kojima T, Matsuo H, Matsuda Y (2000) Inorg Chim Acta 300–302:661–667

    Article  Google Scholar 

  28. Kojima T, Matsuda Y (1999) Chem Lett 81–82

    Google Scholar 

  29. Bagno A, Bonchio M, Sartorel A, Scorrano G (2000) Eur J Inorg Chem 17–20

    Google Scholar 

  30. Yamaguchi M, Kousaka H, Yamagishi T (1997) Chem Lett 769–770

    Google Scholar 

  31. Bakke JM, Frøhaug AEJ (1996) Phys J Org Chem 9:507–513

    Article  CAS  Google Scholar 

  32. Bakke JM, Frøhaug AEJ (1996) Phys J Org Chem 9:310–318

    Article  CAS  Google Scholar 

  33. Bakke JM, Frøhaug AE (1994) Acta Chem Scand 48:160–164

    Article  CAS  Google Scholar 

  34. Kojima T (1996) Chem Lett 121–122

    Google Scholar 

  35. Bressan M, Forti L, Morvillo A (1993) Inorg Chim Acta 211:217–220

    Article  CAS  Google Scholar 

  36. Lau TC, Mak CK (1995) J Chem Soc Chem Comm 943–944

    Google Scholar 

  37. Lau TC, Mak CK (1993) J Chem Soc Chem Commun 766–767

    Google Scholar 

  38. Murahashi SI, Naota T, Hirai NJ (1993) J Org Chem 58:7318–7319

    Article  CAS  Google Scholar 

  39. Murahashi SI, Oda Y, Naota TJ (1992) J Am Chem Soc 114:7913–7914

    Article  CAS  Google Scholar 

  40. Bressan M, Morvillo A, Romanello GJ (1992) J Mol Catal 77:283–288

    Article  CAS  Google Scholar 

  41. Taqui Khan MM, Chatterjee D, Kumar SS, Rao AP, Khan NHJ (1992) J Mol Catal 75:L49–L52

    Article  Google Scholar 

  42. Ohtake H, Higuchi T, Hirobe MJ (1992) J Am Chem Soc 114:10660–10662

    Article  CAS  Google Scholar 

  43. Bressan M, Morvillo AJ (1992) J Mol Catal 71:149–155

    Article  CAS  Google Scholar 

  44. Che CM, Yam VWW, Mak TCW (1990) J Am Chem Soc 112:2284–2291

    Article  CAS  Google Scholar 

  45. Taqui Khan MM, Shukla RSJ (1992) J Mol Catal 77:221–228

    Article  Google Scholar 

  46. Taqui Khan MM, Shukla RS, Rao AP (1989) Inorg Chem 28:452–458

    Article  Google Scholar 

  47. Bakke JM, Braenden JE (1991) Acta Chem Scand 45:418–423

    Article  CAS  Google Scholar 

  48. Bakke JM, Lundquist M (1986) Acta Chem Scand B40:430–433

    Article  CAS  Google Scholar 

  49. Lam WWY, Lee MFW, Lau TC (2006) Inorg Chem 45:315–321

    Article  CAS  Google Scholar 

  50. Guimaraes CA, de Moraes M (2004) Appl Catal 258A:73–81

    Google Scholar 

  51. Chatterjee D, Mitra A, Shepherd RE (2004) Inorg Chim Acta 357:980–990

    Article  CAS  Google Scholar 

  52. d’Alessandro N, Liberatore L, Tonucci L, Morvillo A, Bressan M (2001) New J Chem 25:1319–1324

    Article  CAS  Google Scholar 

  53. Marr SB, Carvel RO, Richens DT, Lee HJ, Lane M, Stavropoulos P (2000) Inorg Chem 39:4630–4638

    Article  CAS  Google Scholar 

  54. Matsumoto Y, Asami M, Hashimoto M, Misono MJ (1996) J Mol Catal 114A:161–168

    Google Scholar 

  55. Higuchi T, Hirobe MJ (1996) J Mol Catal 113A:403–422

    Google Scholar 

  56. Taqui Khan MM, Chatterjee D, Rao AP, Mehta SH (1992) Indian J Chem 31A:146–151

    Google Scholar 

  57. Taqui Khan MM, Rao AP, Bhatt SDJ (1992) J Mol Catal 75:129–139

    Article  Google Scholar 

  58. Taqui Khan MM (1992) Indian J Technol 30:137–144

    Google Scholar 

  59. Taqui Khan MM, Rao AP, Bhatt SD, Merchant RRJ (1990) J Mol Catal 62:265–276

    Article  Google Scholar 

  60. Che CM, Tang WT, Wong WT, Lai TFJ (1990) J Am Chem Soc 111:9048–9056

    Article  Google Scholar 

  61. Lau TC, Che CM, Lee WO, Poon CK (1988) J Chem Soc Chem Commun 1406–1407

    Google Scholar 

  62. Dolphin D, James BR, Leung TW (1983) Inorg Chim Acta 79:25–27

    Article  Google Scholar 

  63. Murahashi SI, Oda Y, Komiya N, Naota T (1994) Tetrahedron Lett 35:7953–7956

    CAS  Google Scholar 

  64. Moody CJ, O’Connell JL (2000) Chem Commun 1311–1312

    Google Scholar 

  65. Komiya N, Noji S, Murahashi SI (2001) Chem Commun 65–66

    Google Scholar 

  66. Sicinski RR, DeLuca HF (1995) Bioinorg Med Chem Lett 5:159–162

    Article  CAS  Google Scholar 

  67. Piatak DM, Ekundayo O (1973) Steroids 21:475–481

    Article  CAS  Google Scholar 

  68. Lee JS, Cao H, Fuchs PLJ (2007) J Org Chem 72:5820–5823

    Article  CAS  Google Scholar 

  69. Tenaglia A, Terranova E, Waegell BJ (1992) J Org Chem 57:5523–5528

    Article  CAS  Google Scholar 

  70. Tenaglia A, Terranova E, Waegell B (1990) J Chem Soc Chem Commun 1344–1345

    Google Scholar 

  71. Mueller RH, DiPardo RM (1975) J Chem Soc Chem Commun 1975, 565–566

    Google Scholar 

  72. Tenaglia A, Terranova E, Waegell B (1991) Tetrahedron Lett 32:1169–1170

    Article  CAS  Google Scholar 

  73. Tenaglia A, Terranova E, Waegell B (1990) Tetrahedron Lett 31:1157–1158

    Article  CAS  Google Scholar 

  74. Tenaglia A, Terranova E, Waegell B (1989) Tetrahedron Lett 30:5275–5276

    Article  CAS  Google Scholar 

  75. Wolff ME, Kerwin JF, Owings FF, Lewis BB, Blank BJ (1963) J Org Chem 28:2729–2734

    Article  CAS  Google Scholar 

  76. Wolff ME, Kerwin JF, Owings FF, Lewis BB, Blank B, Magnani A, Georgian VJ (1960) J Am Chem Soc 82:4117–4118

    Article  CAS  Google Scholar 

  77. Waldmann H, Peng-Yu H, Tan H, Arve L, Arndt H-D (2008) Chem Commun 5562–5564

    Google Scholar 

  78. Deng G, Zhao L, Li C-J (2008) Angew Chem Int Edit 47:6278–6282

    Article  CAS  Google Scholar 

  79. Möhrle H, Azopdi K (2006) Pharmazie 61:815–822

    Google Scholar 

  80. Chatterjeea D, Mitra A, Roy BCJ (2000) J Mol Catal 161A:17–21

    Google Scholar 

  81. Appelbaum L, Heinrichs C, Demtschuk J, Michman M, Oron M, Schäfer HJ, Schumann HJ (1999) Organomet Chem 592:240–250

    Article  CAS  Google Scholar 

  82. El-Hendawy AM, Al-Kubaisi AH, Al-Madfa HA (1997) Polyhedron 16:3039–3045

    Article  CAS  Google Scholar 

  83. Klement I, Lütjens H, Knochel P (1997) Angew Chem Int Edit 36:1454–1456

    Article  CAS  Google Scholar 

  84. Groves JT, Bonchio M, Carofiglio T, Shalyaev KJ (1996) J Am Chem Soc 118:8961–8962

    Article  CAS  Google Scholar 

  85. Cheng WC, Yu WY, Li CK, Che CMJ (1995) J Org Chem 60:6840–6846

    Article  CAS  Google Scholar 

  86. Li CK, Che CM, Tong WF, Tang WT, Wong KY, Lai TF (1992) J Chem Soc Dalton Trans 2109–2116

    Google Scholar 

  87. Coudret JL, Waegell B (1994) Inorg Chim Acta 222:115–122

    Article  CAS  Google Scholar 

  88. Goldstein AS, Beer RH, Drago RSJ (1994) J Am Chem Soc 116:2424–2429

    Article  CAS  Google Scholar 

  89. Cheng WC, Yu WY, Cheung KK, Che CM (1994) J Chem Soc Chem Commun 1063–1064

    Google Scholar 

  90. Upadhyay MJ, Bhattacharya PK, Ganeshpure PA, Satish SJ (1993) J Mol Catal 80:1–9

    Article  CAS  Google Scholar 

  91. Taqui Khan MM, Shukla RSJ (1992) J Mol Catal 71:157–175

    Article  Google Scholar 

  92. Taqui Khan MM, Rao AP, Bhatt SDJ (1992) J Mol Catal 75:41–51

    Article  Google Scholar 

  93. Che CM, Tang WT, Wong KY, Li CK (1991) J Chem Soc Dalton Trans 3277–3280

    Google Scholar 

  94. Che CM, Ho C, Lau TC (1991) J Chem Soc Dalton Trans 1259–1263

    Google Scholar 

  95. Taqui Khan MM, Merchant RR, Chatterjee D, Bhatt KNJ (1991) J Mol Catal 67:309–315

    Article  Google Scholar 

  96. Che CM, Leung WH, Li CK, Poon CK (1991) J Chem Soc Dalton Trans 379–384

    Google Scholar 

  97. Murahashi SI, Naota T, Komiya N (1995) Tetrahedron Lett 36:8059–8062

    Article  CAS  Google Scholar 

  98. Ho C, Leung WH, Che CM (1991) J Chem Soc Dalton Trans 2933–2939

    Google Scholar 

  99. Goldstein AS, Drago RS (1991) J Chem Soc Chem Commun 21–22

    Google Scholar 

  100. Taqui Khan MM (1991) In: Simandi LI (ed) Dioxygen activation and homogeneous catalytic oxidation. Elsevier Science, Amsterdam, pp 31–56

    Chapter  Google Scholar 

  101. Davis S, Drago RS (1990) J Chem Soc Chem Commun 250–251

    Google Scholar 

  102. Taqui Khan MM, Shukla RSJ (1989) J Mol Catal 51:171–180

    Article  Google Scholar 

  103. Neumann R, Abu-Gnim C (1989) J Chem Soc Chem Commun 1324–1325

    Google Scholar 

  104. Taqui Khan MM, Bajaj HC, Shukla RS, Mirza SAJ (1988) J Mol Catal 45:51–56

    Article  Google Scholar 

  105. Seok W, Dobson JC, Meyer TJ (1988) Inorg Chem 27:3–5

    Article  CAS  Google Scholar 

  106. Che CM, Lai TF, Wong KY (1987) Inorg Chem 26:2289–2299

    Article  CAS  Google Scholar 

  107. Thompson MS, De Giovani WF, Moyer BA, Meyer TJJ (1984) J Org Chem 49:4972–4977

    Article  CAS  Google Scholar 

  108. Stock LM, Tse KT (1983) Fuel 62:974–976

    Article  CAS  Google Scholar 

  109. Thompson MS, Meyer TJJ (1982) J Am Chem Soc 104:5070–5076

    Article  CAS  Google Scholar 

  110. Hosahalli RV, Savanur AP, Nandibewoor ST, Chimatadar SA (2010) Transit Met Chem I35:237–246

    Article  CAS  Google Scholar 

  111. Gore ES (1983) Platinum Met Rev 27:111–125

    CAS  Google Scholar 

  112. Emons CHH, Kuster BFM, Jozef AJM, Vekemans JAJM, Sheldon RA (1991) Tetrahedron Asymmetr 2:359–362

    Article  CAS  Google Scholar 

  113. Carlsen PHJ, Katsuki T, Martin VS, Sharpless KBJ (1981) J Org Chem 46:3936–3938

    Article  CAS  Google Scholar 

  114. Wolfe S, Hasan SK, Campbell JR (1970) J Chem Soc Chem Commun 1420–1421

    Google Scholar 

  115. Ferraz HMC, Longo LS (2003) Org Lett 5:1337–1339

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Imperial College, London, SW7 2AZ, United Kingdom

    Prof. William P. Griffith

Authors
  1. Prof. William P. Griffith
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to William P. Griffith .

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer Netherlands

About this chapter

Cite this chapter

Griffith, W.P. (2009). Oxidation of Alkanes. In: Ruthenium Oxidation Complexes. Catalysis by Metal Complexes, vol 34. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-9378-4_4

Download citation

Publish with us

Policies and ethics

Search

Navigation