Tetrahedron

Iodine (III) mediated acetoxy-lactonization of unsaturated nitriles

M Tiecco, L Testaferri, M Tingoli, D Bartoli

Index: Tiecco, Marcello; Testaferri, Lorenzo; Tingoli, Marco; Bartoli, Donatella Tetrahedron, 1990 , vol. 46, # 20 p. 7139 - 7150

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Citation Number: 28

Abstract

4-Pentenenitriles reacted with PhI (OAc) 2 in acetic acid in the presence of 48% HBF4 at 70° 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 ...