Linear α-olefins from linear internal olefins by a boron-based continuous double-bond isomerization process

Industrial and Engineering Chemistry Research

Volumn 46, Issue 2, 2007, Pages 400-410

  De Klerk, Arno ^a   Hadebe, Siphamandla W ^b   Govender, Jude R ^b   Jaganyi, Deo ^b   Mzinyati, Andile B ^a,b   Robinson, Ross S ^b   Xaba, Nontokozo ^b  

^a SASOL TECHNOLOGY PTY LTD   (South Africa)

^b UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERIZATION; ISOMERS; OLIGOMERS; SOLVENTS; SUBSTITUTION REACTIONS;

ALKYLBORANES; HYDROBORATION; OLIGOMERIZATION; PRODUCT DISTRIBUTION;

OLEFINS;

ISOMERIZATION; ISOMERS; OLEFINS; OLIGOMERS; SOLVENTS; SUBSTITUTION REACTIONS;

EID: 33847125772     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie060476c     Document Type: Article

References (154)

1. Camara Greiner, E. O.; Gubler, R.; Inoguchi, Y. Chemical Economics Handbook Marketing Research Report: Linear Alpha Olefins (May 2004); SRI: Menlo Park, CA, 2004.
2. Process Economics Program Report 12D, Linear Alpha Olefins; SRI: Menlo Park, CA, 2001.
3. Joubert, D. J.; Tincul, I. Ethylene copolymers with Fischer-Tropsch olefins. Macromol. Symp. 2002, 178, 69.
4. 13C NMR study of copolymers of propene with higher l-olefins with new microstructures by ansa-zirconocene catalysts. Macromol. Chem. Phys. 2003, 204, 1738.
5. Sacchi, M. C.; Fortini, F.; Losio, S.; Tritto, I.; Costa, G.; Stagnaro, P.; Tincul, I.; Wahner, U. M. Microstructural characteristics and thermal properties of ansa-zirconocene catalyzed copolymers of propene with higher α-olefins Macromol, Symp. 2004, 213, 57.
6. Tullo, A. H. Confronting chemistry. Linear α-olefins producers are making headway in dealing with their chronic oversupply problems. Chem. Eng. News 2005, 83 (43), 30.
7. Mahomed, H.; Bollmann, A.; Dixon, J. T.; Gokul, V.; Griesel, L.; Grove, C.; Hess, F.; Maumela, H.; Pepler, L. Ethylene trimerisation catalyst based on substituted cyclopentadienes. Appl. Catal., A 2003, 255, 355.
8. Dixon, J. T.; Green, M. J.; Hess, F. M.; Morgan, D. H. Advances in selective ethylene trimerisation - a critical overview. J. Organomet. Chem. 2004, M9, 3641.
9. Overett, M. J.; Blann, K.; Bollmann, A.; Dixon, J. T.; Hess, F. M.; Killian, E.; Maumela, H.; Morgan, D. H.; Neveling, A.; Otto, S. Ethylene trimerisation and tetramerisation catalysts with polar-substituted diphosphinoamine ligands. J. Chem. Soc., Chem. Commun. 2005, 622.
10. Bollmann, A.; Blann, K.; Dixon, J. T.; Hess, F. M.; Killian, E.; Maumela, H.; McGuinness, D. S.; Morgan, D. H.; Neveling, A.; Otto, S.; Overett, M. J.; Slawin, A. M. Z.; Wasserscheid, P.; Kuhlmann, S. Ethylene tetramerization: A new route to produce 1-octene in exceptionally high selectivities. J. Am. Chem. Soc. 2004, 126, 14712.
11. Overett, M. J.; Blann, K.; Bollmann, A.; Dixon, J. T.; Haasbroek, D.; Killian, E.; Maumela, H.; McGuinness, D. S.; Morgan, D. H. Mechanistic investigations of the ethylene tetramerisation reaction. J. Am. Chem. Soc. 2005, 127, 10723.
12. Forlani, O.; Ancillotti, F.; Jóvér, B.; Resofszki, G.; Gáti, G. Industrial scale selective high-temperature conversion of 2-butene to 1-butene. I. Development of catalysts. Appl. Catal. 1991, 67, 237.
13. Weast, R. C., Ed. CRC Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1988.
14. Dunning, H. N. Review of olefin isomerisation. Ind. Eng. Chem. 1953, 45, 551.
15. Corma, A. Inorganic solid acids and their use in acid catalyzed hydrocarbon reactions. Chem. Rev. 1995, 95, 559.
16. Matuszak, M. P. (Phillips Petroleum). Isomerization of olefinic hydrocarbons. U.S. Patent 2,403,671, July 9, 1946.
17. Ancillotti, F.; Forlani, O.; Jóvér, B.; Resofszki, G.; Gáti, G. Industrial scale selective high-temperature conversion of 2-butene to 1-butene. II. Comparison of catalysts. Appl_Catal. 1991, 67, 249.
18. Gartside, R. J.; Greene, M. I. (ABB Lummus). Process and catalysts for the isomerisation of internal olefins into α-olefins. WO Patent 02 96,-843, Dec 5, 2002.
19. Voge, H. H.; May, N. C. Isomerization equilibria among n-butenes. J. Am. Chem. Soc. 1946, 68, 550.
20. Hall, L. W., Jr.; Thomas, C. L. (Sun Oil Company). Isomerization of non-terminal olefins. U.S. Patent 3,065,281, Nov 20, 1962.
21. Rutkowski, A. J.; Inchalik, E. J.; Schriesheim, A. (Esso Research and Engineering Company). Trialkylborane displacement reactions. U.S. Patent 3,131,225, April 28, 1964.
22. Brown, H. C. Isomerization of internal olefins to terminal olefins. U.S. Patent 3,173,967, March 16, 1965.
23. Brown, H. C. Organic synthesis via boranes; Wiley: New York, 1975.
24. Asinger, F. Mono-olefins chemistry and technology; Pergamon: Oxford, U.K., 1968.
25. Lehmkuhl, H.; Olbrysch, O. Kinetische Untersuchung der isomerisierung von tri-tert-butyl- und tri-2-propylaluminium (Engl. transl. "A kinetic study of the isomerization of tri-tert-butyl- and tri-2-propylaluminum"). Liebigs Ann. Chem. 1973, 715.
26. Allen, R. H.; Lin, R. W.; Overstreet, A. D. (Ethyl Corporation). Continuous process for preparing aluminum alkyls and linear 1-olefins from internal olefins. U.S. Patent 5,274,153, Dec 28, 1993.
27. Köster, R.; Bruno, G. Austausch von Kohlenwasserstoffresten zwischen organischen Aluminium- und Borverbindungen (Engl. transl. "Exchange of hydrocarbon fragments between organic aluminum and boron compounds"). Liebigs Ann. Chem. 1960, 629, 89.
28. Asinger, F.; Fell, B.; Janssen, R.; Zoche, G.; Mueller, E. W.; Korte, F. W. A. G. K. (Shell). Aluminum alkyls from non-alpha olefins. U.S. Patent 3,322,806, May 30, 1967.
29. Armitage, D. A. Organosilanes. In Comprehensive Organometallic Chemistry, Vol. 2; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; pp 1-203.
30. Barry, A. J.; De Pree, L.; Gilkey, J. W.; Hook, D. E. The reaction of olefins and chlorohydrosilanes. J. Am. Chem. Soc. 1947, 69, 2916.
31. Selin, T. G.; West, R. Stereochemistry and mechanism of silane addition to olefins. I. Addition of trichlorosilane to 1-methylcyclohexene under free radical and thermal conditions. J. Am. Chem. Soc. 1962, 84, 1860.
32. Speier, J. L.; Webster, J.; Barnes, G. H. The addition of silicon hydrides to olefinic double bonds. II. The use of group VIII metal catalysts. J. Am. Chem. Soc. 1957, 79, 974.
33. Chalk, A. J.; Harrod, J. F. Homogeneous catalysis. II. The mechanism of the hydrosilation of olefins catalyzed by group VIII metal complexes. J. Am. Chem. Soc. 1965, 87, 16.
34. Speier, J. L. Homogeneous catalysis of hydrosilation by transition metals. Adv. Organomet. Chem. 1979, 17, 407.
35. Jerkunica, J. M.; Traylor, T. G. σ-π Conjugation of carbon-metal bonds. Dehydrometalation of alkylmetal compounds. J. Am. Chem. Soc. 1971, 93, 6278.
36. Janse van Rensburg, W. Contrathermodynamic isomerisation of internal olefins by exploring the migratory aptitude of various substrates. The significance of concurring molecular modelling. Ph.D. Thesis, University of the Orange Free State, Bloemfontein, South Africa, 2001.
37. Senokwane, S. C. Isomerisation of alkenes using metal hydride complexes, M.Sc. dissertation, University of Potchefstroom, Potchefstroom, South Africa, 2003.
38. Waring, C. E. The kinetics of the thermal decomposition of gaseous silicon tetraethyl and silicon tetrapropyl. J. Chem. Soc., Faraday Trans. 1940, 36, 1142.
39. Fritz, G. Formation and properties of carbosilanes. Angew. Chem., Int. Ed. Engl. 1967, 6, 677.
40. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. Progress in hydroformylation and carbonylation. J. Mol. Catal. A 1995, 104, 17.
41. Van der Veen, L. A.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M. Hydroformylation of internal olefins to linear aldehydes with novel rhodium catalysts. Angew. Chem., Int. Ed. 1999, 38, 336.
42. Schwartz, J.; Labinger, J. A. Hydrozirconation: A new transition metal reagent for organic synthesis. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
43. Klazinga, A. H.; Teuben, J. H. Synthesis and properties of dicyclopentadienyltantalum hydride olefin compounds. J. Organomet. Chem. 1978, 157, 413.
44. Kidwell, R. L.; Lynch, G. J. (Monsanto). Terminal olefin preparation. U.S. Patent 4,125,567, Nov. 14, 1978.
45. Johnson, T. H. (Shell). Olefin isomerisation process. U.S. Patent 4,423,276, Dec. 27, 1983.
46. Burgess, K.; Ohlmeyer, M. J. Transition-metal-promoted hydroboration of alkenes, emerging methodology for organic transformations. Chem. Rev. 1991, 91, 1179.
47. Evans, D. A.; Fu, G. C.; Anderson, B. A. Mechanistic study of the rhodium(I)-catalyzed hydroboration reaction. J. Am. Chem. Soc. 1992, 114, 6679.
48. Burgess, K.; Van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Reactions of catecholborane with Wilkinson's catalyst: Implications for transition metal-catalyzed hydroborations of alkenes. J. Am. Chem. Soc. 1992, 114, 9350.
49. Rubina, M.; Rubin, M.; Gevorgyan, V. Catalytic enantioselective hydroboration of cyclopropenes. J. Am. Chem. Soc. 2003, 125, 7198.
50. Moteki, S. A.; Wu, D.; Chandra, K. L.; Reddy, D. S.; Takacs, J. M. TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration. Org. Lett. 2006, 8, 3097.
51. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. Rhodium(I)- and iridium-(I)-catalyzed hydroboration reactions: Scope and synthetic applications. J. Am. Chem. Soc. 1992, 114, 6671.
52. Luna, A. P.; Bonin, M.; Micouin, L.; Husson, H.-P. Reversal of enantioselectivity in the asymmetric rhodium- versus indium-catalyzed hydroboration of meso substrates. J, Am. Chem. Soc. 2002, 124, 12098.
53. Yamamoto, Y.; Fujikawa, R.; Umemoto, T.; Miyaura, N. Indium-catalyzed hydroboration of alkenes with pinacolborane. Tetrahedron 2004, 60, 10695.
54. Burgess, K.; Van der Donk, W. A. Titanium-mediated additions of borohydride to alkenes. J. Am. Chem. Soc. 1994, 116, 6561.
55. Burgess, K.; Van der Donk, W. A. On titanium-promoted hydroborations of alkenes by borohydride and by catecholborane. Organometallics 1994, 13, 3616.
56. He, X.; Hartwig, J. F. True metal-catalyzed hydroboration with titanium. J. Am. Chem. Soc. 1996, 118, 1696.
57. Hartwig, J. F.; Muhoro, C. N. Mechanistic studies of titanocene-catalyzed alkene and alkyne hydroboration: Borane complexes as catalytic intermediates. Organometallics 2000, 19, 30.
58. 4 addition to alkenes. J. Am. Chem. Soc. 1996, 118, 909.
59. Ashby, E. C.; Noding, S. A. Hydrometalation. 3. Hydroalumination of alkenes and dienes catalyzed by transition metal halides. J. Org. Chem. 1979, 44, 4364.
60. Saam, J, C.; Speier, J. L. The addition of silicon hydrides to olefinic double bonds. III. The addition to non-terminal olefins in the presence of chloroplatinic acid. J. Am. Chem. Soc. 1958, 80, 4104.
61. Selin, T. G.; West, R. Stereochemistry and mechanism of silane addition to olefins. II. Chloroplatinic acid-catalyzed addition of trichlorosilane to alkylcyclohexenes. J. Am. Chem. Soc. 1962, 84, 1863.
62. Marchionna, M.; Patrini, R.; Giavazzi, F.; Pecci, G. C. Linear ethers as high quality components for reformulated diesel fuels. Prepr.-Am. Chem. Soc., Div. Pet. Chem. 1996, 41, 585.
63. Patrini, R.; Marchionna, M. (Snamprogetti). Process for the telomerization of conjugated dienes and suitable catalyst therefore. U.S. Patent 5,510,541, April 23, 1996.
64. Patrini, R.; Lami, M.; Marchionna, M.; Benvenuti, F.; Galletti, A. (M. R.; Sbrana, G. Selective synthesis of octadienyl and butenul ethers via reaction of 1,3-butadiene with alcohols catalyzed by homogeneous palladium complexes. J. Mol. Catal. A 1998, 129, 179.
65. Benvenuti, F.; Carlini, C.; Marchionna, M.; Patrini, R.; Galletti, A. M. R.; Sbrana, G. 1,3-Butadiene telomerization with methanol catalyzed by heterogenized palladium(II) complexes anchored to polymer-bound bis(diphenylphosphino)methane moieties. J. Mol. Catal. A 1999, 139, 177.
66. 4 hydrocarbons; DGMK Conference, Munich, Germany, 2004; p 125.
67. Edwards, C. L. Process for producing 1-octene from butadiene. U.S. Patent Application 20050038305, July 9, 2004.
68. Beller, M.; Jackstell, R.; Klein, H.; Rottger, D.; Maschmeyer, D.; Fernandez, S. S. Method for the production of 1-octene by reductive telomerisation. U.S. Patent Application 20050065387, Oct. 28, 2004.
69. Mittal, K. G. Cracking paraffinic hydrocarbons to make alpha olefins - a review. J. Chem. Technol. Biotechnol. 1986, 36, 291.
70. Bonifay, R.; Marcilly, C. Catalytic Cracking. In Petroleum Refining 3, Conversion Processes; Leprince, P., Ed.; Editions Technip: Paris, 2001; pp 169-227.
71. Brois, S. J.; Rutkowski, A. J. (Esso Research and Engineering Company). Reactions of organo boranes. U.S. Patent 3,101,376, Aug. 20, 1963.
72. Chauvel, A.; Lefebvre, G. Petrochemical Processes. Technical and economic characteristics. 1. Synthesis-gas derivatives and major hydrocarbons, 2nd ed.; Editions Technip: Paris, 1989.
73. Rice, F. O. The thermal decomposition of organic compounds from the standpoint of free radicals. I. Saturated hydrocarbons. J. Am. Chem. Soc. 1931, 53, 1959.
74. Dazeley, G. H.; Hall, C. C. Production of olefins by the cracking of Fischer-Tropsch waxes and their conversion into lubricating oils. Fuel 1948, 27, 50.
75. Sanfilippo, D. Dehydrogenation of paraffins. Key technology for petrochemicals and fuels. CATTECH 2000, 4, 56.
76. Thompson, D. T. Homogeneous catalyst for alkane dehydrogenation. Plat. Met. Rev. 1998, 42, 71.
77. Liu, F.; Goldman, A. S.; Efficient thermochemical alkane dehydrogenation and isomerization catalyzed by an iridium pincer complex. J. Chem. Soc., Chem. Commun. 1999, 655.
78. Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. Dehydrogenation of n-alkanes catalyzed by iridium "pincer" complexes. Regioselective formation of α-olefins. J. Am. Chem. Soc. 1999, 121, 4086.
79. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Thermal, catalytic, regiospecific functionalization of alkanes. Science 2000, 287, 1995.
80. Knözinger, H. Dehydration of alcohols on aluminum oxide. Angew. Chem., Int. Ed. Engl. 1968, 7, 791.
81. Pines, H.; Haag, W. O. Alumina: Catalyst and support. I. Alumina, its intrinsic acidity and catalytic activity. J. Am. Chem. Soc. 1960, 82, 2471.
82. Peri, J. B. Infrared and gravimetric study of the surface hydration of γ-alumina. J. Phys. Chem. 1965, 69, 211.
83. Knözinger, H.; Bühl, H.; Kochloefl, K. The dehydration of alcohols on alumina. XIV. Reactivity and mechanism. J. Catal. 1972, 24, 57.
84. Steynberg, A. P., Dry, M. E., Eds. Fischer-Tropsch technology; Elsevier: Amsterdam, 2004.
85. Bolder, F. H. A.; Mulder, H. Dehydration of alcohols in the presence of carbonyl compounds and carboxylic acids in a Fischer-Tropsch hydrocarbons matrix. Appl. Catal., A 2006, 300, 36.
86. De Klerk, A.; Dancuart, L. P.; Leckel, D. O. Chemicals refining from Fischer-Tropsch synthesis; 18th World Petroleum Congress, Johannesburg, South Africa, 2005; CD 185.
87. Rousseau, M. A study of the displacement reaction in the borane induced isomerisation of alkenes. M.Sc. Dissertation, University of Potchefstroom, Potchefstroom, South Africa, 2002.
88. Kriel, F. H. Catalytic isomerisation of internal and terminal alkenes. M.Sc. Dissertation, Rand Afrikaans University, Johannesburg, South Africa, 2002.
89. Mzinyati, A. B. Thermal transformations of trialkylboranes and hydroboration kinetics of functionalised alkenes. M.Sc. Dissertation, University of Natal, Pietermaritzburg, South Africa, 2003.
90. Govender, J. R. Mechanistic and kinetic study of the hydroboration of 1- and 4-octene by dialkylborane dimers. M.Sc. Dissertation, University of Natal, Pietermaritzburg, South Africa, 2003.
91. 11B NMR spectroscopy techniques. M.Sc. Dissertation, University of KwaZulu-Natal, Pietermartizburg, South Africa, 2004.
92. Hadebe, S. W. Synthesis of sulfur- and nitrogen-based boranes and their hydroboration reactions. M.Sc. Dissertation, University of KwaZulu-Natal, Pietermaritzburg, South Africa, 2004.
93. Mahahle, M. M. D. Isomerisation of alkenes using metal carbenes and related transition metal complexes. Ph.D. Thesis, University of Potchefstroom, Potchefstroom, South Africa, 2005.
94. Manzini, S. S. Organometallic chemistry of some manganese and zirconium complexes: a green chemistry approach. Ph.D. Thesis, University of the Witwatersrand, Johannesburg, South Africa, 2005.
95. De Klerk, A.; Strauss, H. F. SNDBIP bulletin 8: Minutes and comments on the 2002 technical meeting (FTRC 0334). Sasol Technology internal communication, 2003.
96. Chirik, P. J.; Day, M. W.; Labinger, J. A.; Bercaw, J. E. Alkyl rearrangement processes in organozirconium complexes. Observation of internal alkyl complexes during hydrozirconation. J. Am. Chem. Soc. 1999, 121, 10308.
97. McGregor, C.; Sharrock, C.; Grové, C.; Grause, C.; Naudé, H. Sasol's ModCo technology for the production of detergent-range alcohols; Proceedings of the SA Chemical Engineering Congress, Durban, South Africa, 2006; OralCEF18.
98. Balzhiser, R. E.; Samuels, M. R.; Eliassen, J. D. Chemical Engineering Thermodynamics. The study of energy, entropy, and equilibrium; Prentice Hall: Englewood Cliffs, NJ, 1972; pp 242-247.
99. Brown, H. C.; Rao, B. C. S. Hydroboration. I. The reaction of olefins with sodium borohydride-aluminum chloride. A convenient route to organoboranes and the anti-Markownikoff hydration of olefins. J. Am. Chem. Soc. 1959, 81, 6423.
100. Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: Ithaca, NY, 1972.
101. Fehlner, T. P. Reactions of borane. II. Absolute rate of the reaction of borane with ethylene in the gas phase. J. Am. Chem. Soc. 1971, 93, 6366.
102. Dewar, M. J. S.; McKee, M. L. Ground states of molecules. 46. MNDO study of hydroboration of alkenes and alkynes. Inorg. Chem. 1978, 17, 1075.
103. Sundberg, K. R.; Graham, G. D.; Lipscomb, W. N. Hartree-Fock minimal and extended basis set and configuration interaction calculations on the hydroboration reaction J. Am. Chem. Soc. 1979, 101, 2863.
104. Whatley, A. T.; Pease, R. N. A kinetic study of the diborane-ethylene reaction. J. Am. Chem. Soc. 1954, 76, 835.
105. Brown, H. C.; Sharp, R. L. Hydroboration. XXIV. Directive effects in the hydroboration of some substituted styrenes. J. Am. Chem. Soc. 1966, 88, 5851.
106. Streitwieser, A.; Verbit, L.; Bittman, R. Stereochemistry of the primary carbon. XVI. Optically active 1-butanol-1-d by hydroboration. J. Org. Chem. 1967, 32, 1530.
107. Pasto, D. J.; Kang, S. Z. Transfer reactions involving boron. XV. A kinetic study of the hydroboration of olefins with monochloroborane. J. Am. Chem. Soc. 1968, 90, 3797.
108. Wang, K. K.; Brown, H. C. Hydroboration kinetics. 6. Hydroboration of alkenes with 9-borabicyclo[3.3.1]nonane dimer and 9-borabicyclo-[3.3.1]nonane- Lewis base complexes in various solvents: An interpretation of the catalytic effect of ether solvents on the hydroboration reaction. J. Am. Chem. Soc. 1982, 104, 7148.
109. Brown, H. C.; Chandrasekharan, J. Hydroboration kinetics. XII. Mechanism of hydroboration of alkenes with borane-Lewis base complexes. Evidence that the mechanism of the hydroboration reaction proceeds through a prior dissociation of such complexes. Can. Chim. Ital. 1987, 117, 517.
110. Pasto, D. J.; Lepeska, B.; Cheng, T.-C. Measurement of the kinetics and activation parameters for hydroboration of tetramethylethylene and measurement of isotope effects in the hydroboration of alkenes. J. Am. Chem. Soc. 1972, 94, 6083.
111. Clark, T.; Wilhelm, D.; Schleyer, P. V. R. Mechanism of hydroboration in ether solvents. A model ab initio study. J. Chem. Soc., Chem. Commun. 1983, 606.
112. Bennett, J. E.; Skinner, H. A. Thermochemistry of organoboron compounds. Part VI. The heats of reaction of diborane with olefins. J. Chem. Soc. 1961, 2472.
113. Brown, H. C.; Rao, B. C. S. Organoboranes. I. Isomerization and displacement reactions of organoboranes. A convenient procedure for the conversion of internal olefins into primary alcohols. J. Am. Chem. Soc. 1959, 81, 6434.
114. Brown, H. C.; Zweifel, G. Isomerization of organoboranes derived from branched-chain and ring olefins-further evidence for the elimination-addition mechanism of isomerization. J. Am. Chem. Soc. 1960, 82, 1504.
115. Williams, R. E. Mechanism of alkylborane isomerization. Inorg. Chem. 1962, 1, 971.
116. Hennion, G. F.; McCusker, P. A.; Ashby, E. C.; Rutkowski, A. J. Organoboron compounds. VI. Isomerization of boranes containing secondary and tertiary alkyl groups. J. Am. Chem. Soc. 1957, 79, 5190.
117. Wood, S. E.; Rickborn, B. Stereoselectivity in organoborane rearrangement: Relationship to the mechanism of hydroboration. J. Org. Chem. 1983, 48, 555.
118. Brown, H. C.; Zweifel, G. Organoboranes. III. Isomerization of organoboranes derived from the hydroboration of acyclic olefins. J. Am. Chem. Soc. 1966, 88, 1433.
119. Brown, H. C.; Bhatt, M. V. Organoboranes. IV. The displacement reaction with organoboranes derived from the hydroboration of branched-chain olefins. A contrathermodynamic isomerization of olefins. J. Am. Chem. Soc. 1966, 88, 1440.
120. Rickborn, B.; Wood, S. E. Cleavage of cyclopropanes by diborane. J. Am. Chem. Soc. 1971, 93, 3940.
121. Field, L. D.; Gallagher, S. P. The stereochemistry of the hydroboration rearrangement. Tetrahedron Lett. 1985, 26, 6125.
122. Brown, H. C.; Zweifel, G. Hydroboration. VII. Directive effects in the hydroboration of olefins. J. Am. Chem. Soc. 1960, 82, 4708.
123. Parsons, T. D.; Ritter, D. M. Alkenylmethylborines. J. Am. Chem. Soc. 1954, 76, 1710.
124. Brown, H. C. Hydroboration; Benjamin: New York, 1962.
125. Köster, R. Transformations of organoboranes at elevated temperatures. Angew. Chem., Int. Ed. Engl. 1964, 3, 174.
126. Midland, M. M.; Tramontane, A.; Zderic, S. A. The reaction of B-alkyl-9-borabicyclo[3.3.1]nonanes with aldehydes and ketones. A facile elimination of the alkyl group by aldehydes. J. Organomet. Chem. 1978, 156, 203.
127. Midland, M. M.; Petre, J. E.; Zderic, S. A.; Kazubski, A. Thermal reactions of B-Alkyl-9-borabicyclo[3.3.1]nonane (9-BBN). Evidence for unusually facile dehydroboration with B-pinanyl-9-BBN. J. Am. Chem. Soc. 1982, 104, 528.
128. Rossi, F. M.; McCusker, P. A.; Hennion, G. F. Organoboron compounds. XIX. Kinetics of the thermal isomerization of α-branched trialkylboranes. J. Org. Chem. 1967, 32, 450.
129. Cocks, A. T.; Eggers, K. W. Reactions of group III metal alkyls in the gas phase. Part VII. The thermal unimolecular decomposition of triisobutylboron. J. Chem. Soc. A 1971, 3606.
130. Hurd, D. T. The reactions of diborane with hydrocarbons. J. Am. Chem. Soc. 1948, 70, 2053.
131. Brown, H. C.; Rao, B. C. S. Hydroboration. II. A remarkably fast addition of diborane to olefins-scope and stoichiometry of the reaction. J. Am. Chem. Soc. 1959, 81, 6428.
132. Brown, H. C.; Zweifel, G. Organoboranes. VI. Isomerization of organoboranes derived from the hydroboration of cyclic and bicyclic olefins. J. Am. Chem. Soc. 1967, 89, 561.
133. Rutkowski, A. J. The olefin displacement reaction of trialkylboranes. Prepr.-Am. Chem. Soc., Div. Pet. Chem. 1963, 8, B13.
134. Taylor, M. D.; Grant, L. R.; Sands, C. A. A convenient preparation of pyridine-borane. J. Am. Chem. Soc. 1955, 77, 1506.
135. Ashby, E. C. New syntheses of trialkylboranes. J. Am. Chem. Soc. 1959, 81, 4791.
136. Clay, J. M.; Vedejs, E. Hydroboration with pyridine borane at room temperature. J. Am. Chem. Soc. 2005, 127, 5766.
137. Graham, W. A. G.; Stone, F. G. A. The relative stabilities of some molecular addition compounds of boron. J. Inorg. Nucl. Chem. 1956, 3, 164.
138. Young, D. E.; McAchran, G. E.; Shore, S. G. Boron heterocycles. III. The effect of borane Lewis acid on apparent base strength. New examples of base strength reversal. J. Am. Chem. Soc. 1966, 88, 4390.
139. Huheey, J. E. Inorganic Chemistry. Principles of structure and reactivity, 3rd ed.; Harper and Row: New York, 1983; pp 312-325.
140. Brown, H. C.; Mandal, A. K. Hydroboration. 88. Borane-1,4-thioxane. A new convenient hydroborating agent for the preparation of representative borane reagents. J. Org. Chem. 1992, 57, 4970.
141. 11B NMR Spectroscopy. Unpublished results, University of KwaZulu-Natal, Pietermaritzburg, South Africa.
142. Hadebe, S. W.; Robinson, R. S. Microwave mediated rhodium-catalyzed hydroboration of trans-4-octene with pinacolborane. Tetrahedron Lett. 2006, 47, 1299.
143. Lane, C. F. Organic synthesis using borane-methyl sulfide. The hydroboration-oxidation of alkenes. J. Org. Chem. 1974, 39, 1437.
144. Winternitz, P. F.; Carotti, A. A. The thermal decomposition of trialkylboranes. J. Am. Chem. Soc. 1960, 82, 2430.
145. Brown, H. C.; Murray, K. J.; Müller, H.; Zweifel, G. Organoboranes. V. The thermal cyclization of dialkylboranes. A convenient synthesis of 2,4,4-trimethyl-1,5-pentanediol and related 1,5-diols. J. Am. Chem. Soc. 1966, 88, 1443.
146. Köster, R.; Larbig, W.; Rotermund, G. W. Pyrolysis of alkyl- and cycloalkylboranes. (In Ger.) Liebigs Ann. Chem. 1965, 682, 21.
147. Ramp, F. L.; DeWitt, E. J.; Trapasso, E. Homogeneous hydrogenation catalyzed by boranes. J. Org. Chem. 1962, 27, 4368.
148. Mzinyati, A. B. Unpublished results, University of KwaZulu-Natal, Pietermaritzburg, South Africa.
149. Itoh, M.; Arase, A.; Suzuki, K.; Suzuki, A. Isomerization of internal olefins to α-olefins via hydroboration. I. Isomerization of 2-pentene to the 1-pentene isomer via hydroboration. Kogyo Kagaku Zasshi 1968, 71, 1653 (in Japanese).
150. Rosenblum, L. The thermal decomposition of tri-n-butylborane. J. Am. Chem. Soc. 1955, 77, 5016.
151. Taniguchi, H. An examination of the displacement reactions in alkyldicyclohexylborane and alkyldi-exo-norbornylborane. Bull. Chem. Soc. Jpn. 1979, 52, 2942.
152. Brown, H. C.; Bhatt, M. V.; Munekata, T.; Zweifel, G. Organoboranes. VII. The displacement reaction with organoboranes derived from the hydroboration of cyclic and bicyclic olefins. Conversion of endocyclic to exocyclic double bonds. J. Am. Chem. Soc. 1967, 89, 567.
153. Brown, H. C.; Moerikofer, A. W. Hydroboration. XV. The influence of structure on the relative rates of hydroboration of representative unsaturated hydrocarbons with diborane and with bis-(3-methyl-2-butyl)-borane. J. Am. Chem. Soc. 1963, 85, 2063.
154. Brown, H. C.; Liotta, R.; Scouten, C. G. Hydroboration. 43. Effect of structure on the reactivity of representative olefins toward hydroboration by 9-borabicyclo[3.3.1]nonane. J. Am. Chem. Soc. 1976, 98, 5297.