Reduction of an hexamethylphosphoramide degradation product: A diazabutadiene

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4564-4567

  Rose, Brad D ^a   Peters, Steven J ^a   Reiter, Richard C ^a   Stevenson, Cheryl D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

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Indexed keywords

EID: 70349915934     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901798s     Document Type: Article

References (20)

1. Weak versions of this spectrum were observed during over-reduction experiments in the following studies: (a) Peters, S. J.; Turk, M. R.; Kiesewetter, M. K.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 11212-11268.
2. (b) Gard, M. N.; Kiesewetter, M. K.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 16143-16150.
3. Ion association is absent with anion radicals in HMPA. See: (a) Levin, G.; Jagur-Grodzinski, J.; Szwarc, M. J. Am. Chem. Soc. 1970, 92, 2268-2275.
4. (b) Stevenson, C. D.; Echegoyen, L.; Lizardi, L. R. J. Phys. Chem. 1972, 76, 1439-1442.
5. This spectrum causes consternation, as its appearance means that you have over-reduced and can no longer observe the desired radical.
6. Piette, L. H.; Ludwig, P.; Adams, R. N. J. Am. Chem. Soc. 1962, 84, 4212-4215.
7. (a) Liu, R. Huaxue Shijie 1991, 32, 154-155.
8. (b) Kenneth, G. L. Amidation of phosphorus halides with organic amines, US Patent 2,852,550, 1958.
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11. (b) Engels, B. Calculation of NMR and EPR Parameters Theory and Applications; Kaup, M., Buhl, M., Malkin, V. G., Eds.; Wiley-VCH: Weinheim, 2004; pp 483-492.
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14. (a) Wertz, J. E.; Bolton, J. R. Electron Spin Resonance; McGraw-Hill: New York, 1986; pp 58-60.
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16. (c) See also: Wiberg, K. B.; Rablen, P. R.; Marquez, M. J. Am. Chem. Soc. 1992, 114, 8654-8668.
17. Franz, K. D.; Dieck, T. H.; Starzewski, K. A. O.; HohMann, F. Tetrahedron 1975, 31, 1465-1469.
18. (a) For example, see: Tuononen, H. M.; Armstrong, A. F. Inorg. Chem. 2005, 44, 8277-8284, and references therein.
19. (b) Schmidt, E. S.; Jockisch, A.; Schmidbaur, H. J. Am. Chem. Soc. 1999, 121, 9758-9759.
20. (c) Andappan, M. M. S.; Nilsson, P.; von Schenck, H.; Larhed, M. J. Org. Chem. 2004, 69, 5212-5218.