FIGR ID=jo070130rn00002> figures/jo070130rn00002.gif" ALIGN="left" HSPACE=5> |
Organotri
fluoroborates are robust reagents capable o
f withstanding ozonolysis o
f remote alkenes, thus providing a newroute to oxo-substituted organotri
fluoroborates. The primaryozonides initially generated upon ozonolysis can be reducedwith Zn/AcOH to a
fford the carbonyl compounds. Alternatively, capture o
f the carbonyl oxides with either an appropriate
N-oxide or H
2O easily gives the desired oxo-substituted organotri
fluoroborates. Both unsaturated alkyltri
fluoroborates and aryltri
fluoroborates e
ffectively participatein the reaction. The process provides oxo-
functionalizedorganotri
fluoroborates that cannot be prepared directly viaeither transmetalation or hydroboration protocols.
