Barton DH. R.
*
McCombie SW.
* Imperial College London, UK
A New Method for the Deoxygenation of Secondary Alcohols.
J. Chem. Soc., Perkin Trans. 1 1975;
16: 1574-1585
Key words
deoxygenation - secondary alcohols - stannanes
Significance
The authors reported a very broadly applicable method for the deoxygenation of secondary alcohols, providing complex hydrocarbons in high yields. The alcohol thereby has to be activated by transforming it into its corresponding thioester.
Comment
By using a radical mechanism and the favorable formation of an S–Sn bond, these thioesters can be deoxygenated. This concept has been revived in the Barton–McCombie decarboxylation (J. Chem. Soc., Chem. Commun.
1980, 15, 732).
