Conversion of Alkyl Halides into Alcohols Using a Near Stoichiometric Amount of Molecular Oxygen: An Efficient Route to 18O- And 17O-Labeled Alcohols

Synlett

Volumn 1997, Issue 7, 1997, Pages 801-802

  Sawamura, Masaya ^a   Kawaguchi, Yasuhide ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000780005     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5779     Document Type: Article

References (16)

1. Battino, R.; Rettich, T. R.; Tominaga, T. J. Phys. Chem. Ref. Data 1983 12, 163.
2. The common sources of oxygen isotopes are molecular oxygen and water, which are normally used in excess or introduced through multi-step procedures, and the synthetic transformations are not necessarily effcient; for example, see: (a) Schöttler, M.; Boland, W. Synlett 1997, 91. (b) Sowa, G. A.; Hengge, A. C.; Cleland, W. W. J. Am. Chem. Soc. 1997, 119, 2319.
3. The common sources of oxygen isotopes are molecular oxygen and water, which are normally used in excess or introduced through multi-step procedures, and the synthetic transformations are not necessarily effcient; for example, see: (a) Schöttler, M.; Boland, W. Synlett 1997, 91. (b) Sowa, G. A.; Hengge, A. C.; Cleland, W. W. J. Am. Chem. Soc. 1997, 119, 2319.
4. Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1991, 113, 8980.
5. 4. See: Mayer, S.; Prandi, J. Tetrahedron Lett. 1996, 37, 3117.
6. For a related halide-to-alcohol conversion, see: Barrett, A. G.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837.
7. Two equivalents of the reagent may be stoichiometric, since the use of less reagent results in lower yield (i.e., only a single hydride used for reduction).
8. For the use of a catalytically generated tin hydride for reduction, see: Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554.
9. 3CN in the expense of some increase of the simple reduction product (3a).
10. Hence, the presence of AIBN was not mandatory, though it greatly accelerated the reaction.
11. Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095.
12. Neumann, W. P. Synthesis 1987, 665.
13. 2 and t-BuMgBr: Davies, A. G.; Muggleton, B.; Robberts, B. P.; Tse, M-W.; Winter, J. N. J. Organomet. Chem. 1976, 118, 289.
14. 2(t-Bu)SnCl, see: Nakamura, E.; Sato, K.; Imanishi, Y. Synlett 1995, 525.
15. Riess, J. G.; Le Blanc, M. Angew. Chem. Int. Ed. Engl. 1978, 17, 621, etc.
16. 18O. Unlabeled alcohol was not detected by GC-Mass (El).