Activation and Transfer of Nitrogen from a Nitridomanganese(V) Porphyrin Complex. The Aza Analogue of Epoxidation

Journal of the American Chemical Society

Volumn 105, Issue 7, 1983, Pages 2073-2074

  Groves, John T ^a   Takahashi, Tadashi ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845552528     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00345a071     Document Type: Article

References (18)

1. Groves, J.T.; Nemo, T.E.; Myers, R.S. J. Am. Chem. Soc. 1979, 101, 1032-1033.
2. (a) Groves, J.T.; Kruper, W. J., Jr. J. Am. Chem. Soc. 1979, 101, 7613-7615; (b) Groves, J.T.; Kruper, W.J., Jr.; Haushalter, R.D.J. Am. Chem. Soc. 1980, 102, 6375-6377. (c) Groves, J.T.; Haushalter, R.C.; Nakamura, M.; Nemo, T.E.; Evans, B.J.J. Am. Chem. Soc. 1981, 103, 2884-2886. (d) Groves, J.T.; Nemo, T.E. submitted for publication in J. Am. Chem. Soc.
3. Hill, C.L.; Schardt, B.C. J. Am. Chem. Soc. 1980, 102, 6374-6375.
4. Chang, C.K.; Kuo, M.-S. J. Am. Chem. Soc. 1979, 101, 3413-3415.
5. (a) Hentges, G.S.; Sharpless, K.B. J. Org. Chem. 1980, 45, 2257-2259; (b) Herranz, E.; Sharpless, K.B.J. Org. Chem. 1978, 43, 2544-2548; (c) Sharpless, K.B.; Patrick, D.W.; Truesdale, L.K.; Biller, S.A.J. Am. Chem. Soc. 1975, 97, 2305-2307.
6. Antipas, A.; Buchler, J.W.; Gouterman, M.; Smith, P.D. J. Am. Chem. Soc. 1980, 102, 198-207.
7. Dehnicke, K.; Prinz, H.; Kafiz, W.; Kujanek, R. Liebigs Ann. Chem. 1981, 20-27.
8. Groves, J.T.; Takahashi, T.; Butler, W.M. Inorg. Chem., in press.
9. (a) Arshankan, S.I.; Poznjak, A.L.Z. Anorg. Allg. Chem. 1982, 481, 201-6. (b) Buchler, J.W.; Dreher, C.; Lay, L.K.Z. Naturforsch., B 1982., 37, 1155-62. (c) Hill, C.L.; Hollander, F.J.J. Am. Chem. Soc. 1982, 104, 7318-7319.
10. Mansuy, D.; Battioni, P.; Mahy, J.P. J. Am. Chem. Soc. 1982, 104, 4487-4489.
11. For an example of alkane amidation See: Breslow, R.; Gellman, S.H.J. Chem. Soc, Chem. Commun. 1982, 1400-1401.
12. -1, (b) Preliminary X-ray data for 1 confirm the assigned structure: Yamauchi, M.; Butler, W.; unpublished results.
13. An acylnitrenomanganese(III) structure or a nitrogen-bridged species would be functionally equivalent to 2; Callot, H.J.; Chevier, B.; Weiss, R. J. Am. Chem. Soc. 1978, 100, 4733-4741.
14. Shimomura, E.T.; Phillippi, M.A.; Goff, H.M.; Scholz, W.F.; Reed, C.A. J. Am. Chem. Soc. 1981, 103, 6778.
15. Wayland, B.B.; Olson, L.W.; Siddiqui, Z.U. J. Am. Chem. Soc. 1976, 98, 94-98.
16. for reviews of nitrene reactions See: Lwowski, W., Ed. “Nitrenes,” Wiley: New York, 1970.
17. (a) Hassner, A.; Matthews, G.J.; Fowler, F.W. J. Am. Chem. Soc. 1969, 91, 5046-5054. (b) Fowler, F.W.; Hassner, A.; Levy, L.A.J. Am. Chem. Soc. 1967, 89, 2077-2082.
18. The synthetic scope of this reaction is under current investigation. Cyclooctene is at present the most favorable case.