
Tetrahedron p. 7139 - 7150 (1990)
Update date:2022-08-02
Topics:
Tiecco, Marcello
Testaferri, Lorenzo
Tingoli, Marco
Bartoli, Donatella
4-Pentenenitriles reacted with PhI(OAc)2 in acetic acid, in the presence of 48percent HBF4, at 70 deg C, to afford the dihydro-5-acetoxymethyl-2(3H)-furanones in good yields.Similarly, 3-butenenitriles gave the dihydro-4-acetoxy-2(3H)-furanones, although in lower yields.Parallel experiments showed that, under the same conditions, 4-pentenoic and 3-pentenoic acids reacted much more easily and gave the same acetoxy-lactonization process at room temperature.
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