Nitridomanganese(V) Complexes: Design, Preparation, and Use as Nitrogen Atom-Transfer Reagents

Accounts of Chemical Research

Volumn 30, Issue 9, 1997, Pages 364-372

  Du Bois, J ^a,d,e   Tomooka, Craig S ^a,f   Hong, Jason ^a,c   Carreira, Erick M ^a,b,c  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c HARVARD UNIVERSITY   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^f UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001578860     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960222v     Document Type: Article

References (91)

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38. (salen)Mn(N) = nitrido[N,N′-ethylenebis(salicylideneaminato)]-manganese(V); (saltmen)Mn(N) = nitrido[N,N′-(1,1,2,2-tetramethyl)-ethylenebis(salicylideneaminato)] manganese(V).
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41. The nature of this dark brown Mn(III) species has not been established and is drawn as such for convenience.
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43. Mn≡N distances of 1.51 Å have been reported for (TpMPP)Mn(N) and (OEP)Mn(N); see refs 10b and 10c, respectively.
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45. The figure shown was drawn using the SPARTAN program and is an exact representation of the X-ray crystal structure.
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58. For leading references on the preparation of 2-amino sugars, see: (a) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. (b) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9526. (c) Leblanc, Y.; Labelle, M. In Cycloaddition Reactions in Carbohydrate Chemistry; Giuliano, R. M., Ed.; ACS Symposium Series; American Chemical Society: Washington, DC, 1990; Vol. 494, p 81.
59. For leading references on the preparation of 2-amino sugars, see: (a) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. (b) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9526. (c) Leblanc, Y.; Labelle, M. In Cycloaddition Reactions in Carbohydrate Chemistry; Giuliano, R. M., Ed.; ACS Symposium Series; American Chemical Society: Washington, DC, 1990; Vol. 494, p 81.
60. For leading references on the preparation of 2-amino sugars, see: (a) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. (b) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9526. (c) Leblanc, Y.; Labelle, M. In Cycloaddition Reactions in Carbohydrate Chemistry; Giuliano, R. M., Ed.; ACS Symposium Series; American Chemical Society: Washington, DC, 1990; Vol. 494, p 81.
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63. 3CON may be transferred to 3,4-dihydro-2H-pyran (45-50% yield) by following a previously described protocol (see ref 17). Under identical conditions, no reaction was observed when tri-O-benzylglucal was employed as the substrate.
64. Mansuy, D.; Battioni, P.; Mahy, J.-P. J. Am. Chem. Soc. 1982, 104, 4487. Also, see: Mahy, J.-P.; Battioni, P.; Mansuy, D.; Fisher, J.; Weiss, R.; Mispelter, J.; Morgenstern-Badarau, I.; Gans, P. J. Am. Chem. Soc. 1984, 106, 1699.
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69. III(salen) dimer has also been crystallographically characterized, see: Nichols, P. J.; Fallon, G. D.; Murray, K. S.; West, B. O. Inorg. Chem. 1988, 27, 2795.
70. III(salen) dimer has also been crystallographically characterized, see: Nichols, P. J.; Fallon, G. D.; Murray, K. S.; West, B. O. Inorg. Chem. 1988, 27, 2795.
71. μ-Oxo-bridged Mn dimers have been characterized in reactions with PhI=O, see: (a) Smegal, J. A.; Schardt, B. C.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3510. (b) Smegal, J. A.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3515.
72. μ-Oxo-bridged Mn dimers have been characterized in reactions with PhI=O, see: (a) Smegal, J. A.; Schardt, B. C.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3510. (b) Smegal, J. A.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3515.
73. This assumes that decomposition of the acylated nitrido species 17 does not occur through intramolecular processes. (a) Mahy, J.-P.; Battioni, P.; Bedi, G.; Mansuy, D.; Fisher, J.; Weiss, R.; Morgenstern-Badarau, I. Inorg. Chem. 1988, 27, 353. (b) Mahy, J.-P.; Battioni, P.; Mansuy, D. J. Am. Chem. Soc. 1986, 108, 1079.
74. This assumes that decomposition of the acylated nitrido species 17 does not occur through intramolecular processes. (a) Mahy, J.-P.; Battioni, P.; Bedi, G.; Mansuy, D.; Fisher, J.; Weiss, R.; Morgenstern-Badarau, I. Inorg. Chem. 1988, 27, 353. (b) Mahy, J.-P.; Battioni, P.; Mansuy, D. J. Am. Chem. Soc. 1986, 108, 1079.
75. An analogous, slow addition procedure is typically used for alkene cyclopropanation; see ref 32b.
76. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179.
77. N-Carbomethoxy aziridines generated from glycals have been shown to react with alcohols to give methyl glycoside products, see: Kozlowska-Gramsz, E.; Descotes, G. Can. J. Chem. 1982, 60, 558.
78. A similar strategy has been successfully employed to inhibit the dimerization reaction of metal-oxo species, see: (a) Momenteau, M.; Reed, C. A. Chem. Rev. (Washington, D.C.) 1994, 94, 659. (b) Collman, J. P.; Gagne, R. R.; Halbert, T. R.; Marchon, J.-C.; Reed, C. A. J. Am. Chem. Soc. 1973, 95, 7868.
79. A similar strategy has been successfully employed to inhibit the dimerization reaction of metal-oxo species, see: (a) Momenteau, M.; Reed, C. A. Chem. Rev. (Washington, D.C.) 1994, 94, 659. (b) Collman, J. P.; Gagne, R. R.; Halbert, T. R.; Marchon, J.-C.; Reed, C. A. J. Am. Chem. Soc. 1973, 95, 7868.
80. H-3R-sal-R′ is used to designate substitution on the salicylimine, as shown in Figure 9.
81. For elegant studies of electronic tuning in metal catalysts, see: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309.
82. For elegant studies of electronic tuning in metal catalysts, see: (a) Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703. (b) Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309.
83. (a) Wang, X.; Erickson, S. D.; Iimori, T.; Still, W. C. J. Am. Chem. Soc. 1992, 114, 4128.
84. (b) Iimon, T.; Still, W. C.; Rheingold, A. L.; Staley, D. L. J. Am. Chem. Soc. 1989, 111, 3439.
85. For a comprehensive review on the preparation and characterization of transition-metal nitrido complexes, see: (a) Dehnicke, K.; Strähle, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 955.
86. 2 have also been employed; see refs 10b and 11, respectively.
87. Clemens, D. F.; Woodford, W.; Dellinger, E.; Tyndall, Z. Inorg. Chem. 1969, 8, 998.
88. We have recently communicated this work, see: Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M.; Day M. W. Angew. Chem. 1997, 109, 1772.
89. (a) Collins, T. J.; Powell, R. D.; Slebodnick, C.; Uffelman, E. S. J. Am. Chem. Soc. 1990, 112, 899.
90. The crystals of 45 produced weak data which prevented complete refinement of this structure. However, the overall structure is confirmed.
91. For the synthesis of these ligands, see: Bolm, C.; Wieckhardt, K.; Zehnder, M.; Glasmacher, D. Helv. Chim. Acta 1991, 74, 717.