Journal of Organic Chemistry p. 1004 - 1010 (1994)
Update date:2022-08-04
Topics:
Dittmer, Donald C.
Zhang, Yanzhi
Discordia, Robert P.
Treatment of glycidyl acetates with telluride ion (Te(2-)) produced by reduction of elemental Te with LiEt3BH yields allylic alcohols by loss of the epoxide oxygen atom and the acetyl group from the ester.If the glycidyl acetate is disubstituted at C-3, a rearrangement to an isomeric allylic alcohol competes with the deoxygenation-deacetylation.Triethylborane, a byproduct in the reduction of Te, is believed to play an important role as a Lewis acid since when it is absent or removed by addition of fluoride ion the reaction is extremely slow.
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