DOI: 10.1039/A703156D
(Paper)
Reference Section for: Chem. Commun., 1997, 1509-1510
Unusual generation of methoxy groups in Barton deoxygenations of alcohols
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Caroline S. Bensasson, Sir John Cornforth, Ming-Hui Du and James R. Hanson
Abstract
Reaction of the S-methyl dithiocarbonate of lanosterol with excess of tributyltin deuteride and azoisobutyronitrile in benzene afforded lanosteryl methyl ether in which all hydrogen in the methoxy group originated from the organotin reagent.
References
- D. H. R. Barton and S. W. McCombie, J. Chem. Soc., Perkin Trans. 1, 1975, 1574 RSC.
- D. H. R. Barton, D. Crich, A. Löbberding and S. Z. Zard, J. Chem. Soc., Chem. Commun., 1985, 646 RSC.
- D. H. R. Barton, D. Crich, A. Löbberding and S. Z. Zard, Tetrahedron, 1986, 42, 2329 CrossRef CAS.
- D. H. R. Barton, D. O. Jang and J. C. Jaszberenyi, Tetrahedron Lett., 1990, 31, 3991 CrossRef CAS.
- K. C. Nicolaou, M. Sato, E. A. Theodorakis and N. D. Miller, J. Chem. Soc., Chem. Commun., 1995, 1583 RSC.
- P. J. Barker and A. L. J. Beckwith, J. Chem. Soc., Chem. Commun., 1984, 683 RSC.