Tetrahedron Letters p. 1341 - 1344 (1987)
Update date:2022-08-04
Topics:
Balaban, Teodor-Silviu
Balaban, Alexandru, T.
The major reduction products with triacetoxyborohydride (NaBH4 in AcOH) of 2,4,6-trisubstituted pyrylium salts bearing alkyl substituents in the 2- and/or 6-position are the Δ3-dihydropyrans with cis 2- and 6-substituents and all-cis-2,4,6-trisubstituted tetrahydropyrans. Δ3-dihydropyrans are shown to be formed via 2H-pyrans by a 1,4 reduction while tetrahydropyrans result from 4H-pyrans by reduction of both enol-ether double bonds.
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