Lithium Chromium(I) Dihydride: A Novel Reagent for the Versatile Reductive Metathesis, Reductive Cyclization, Oligomerization, or Polymerization of Diverse Organic Substrates1

Organometallics

Volumn 19, Issue 7, 2000, Pages 1211-1213

  Eisch, John J ^a   Alila, Joseph R ^a  

^a BINGHAMTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001738511     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om991028q     Document Type: Article

References (19)

1. Part 19 of the series Organic Chemistry of Subvalent Transition Metal Complexes. Part 18: Eisch, J. J.; Alila, J. R. Organometallics 1999, 18, 2930.
2. Eisch, J. J.; Shi, X.; Alila, J. R.; Thiele, S. Chem. Ber. / Recl. 1997, 130, 1175.
3. Eisch, J. J.; Shi, X.; Lasota, J. Z. Naturforsch. 1995, 50b, 342.
4. Eisch, J. J.; Pombrik, S. I.; Shi, X.; Wu, S. C. Macromol. Sym. 1995, 89, 221.
5. Eisch, J. J.; Shi, X.; Owuor, F. A. Organometallics 1998, 17, 5219.
6. Eisch, J. J.; Alila, J. R. Organometallics 1999, 18, 2930.
7. Eisch, J. J.; Patel, Y. Unpublished studies. Analogous alkylative reductions are being examined for the salts of vanadium, tungsten, and manganese.
8. Eisch, J. J.; Owuor, F. A.; Shi, X. Organometallics 1999, 18, 1583.
9. -1 (C=C-H stretch).
10. 2 was collected in a gas buret after passage through a cold trap at -78°C and was identified by mass spectrometry.
11. Chromium(II) is known to behave as a one-electron reductant toward allylic or benzylic halides, and thus 6 could transform only 50% of 2 equiv of 7 into 8.
12. -1 to higher frequencies, compared with those of free THF.
13. The isolated 9-deuterated derivative of 9-fluorenol was further-more 65% O-deuterated. That 9-fluorenol was 35% protiated at oxygen can be ascribed to facile H,D-exchange of hydroxyl hydrogen that occurs in moist air upon workup.
14. The authors are grateful for the assistance and the interpretations of Professor David C. Doetschman, director of the NSF Regional Center for Pulsed EPR and Photochemical Studies here at SUNY-Binghamton.
15. Efforts to obtain suitable crystals of 5a for such a structure determination are being pursued in collaboration with the XRD group of Professor Arnold L. Rheingold of the University of Delaware.
16. (a) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3180.
17. (b) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
18. (c) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.
19. (d) Jubert, C.; Nowotny, S.; Kornemann, D.; Antes, I.; Tucker, C. E.; Knochel, P. J. Org. Chem. 1992, 57, 6384.