Abstract
Bis(benzotriazolyl)methylbenzenes
1a,b were converted by excess lithium metal in the presence of ketones into the 1,3-diols
3a-g in moderate to good yields. However, similar treatment of
5 gave only the mono reduction products
6, 7. Compounds
1a,b reacted with 1 equivalent of diketone
8 to form olefins
10a,b.
The umpolung of aromatic aldehydes to gem-dianion synthons was achieved in only two steps by first conversion of the aldehydes to bis(benzotriazolyl) derivatives followed by reductive coupling.