Tetrahedron letters

Thermal and photochemical reactions of biacetyl with 1, 1-diethoxyethene.“Umpolung” of the reactivity of biacetyl by photochemical induced electron transfer.

J Mattay, J Gersdorf, U Freudenberg

Index: Mattay, Jochen; Gersdorf, Joachim; Freudenberg, Ulrich Tetrahedron Letters, 1984 , vol. 25, # 8 p. 817 - 820

Full Text: HTML

Citation Number: 21

Abstract

Abstract The thermal and photochemical reactions of biacetyl 1 and 1, 1-diethoxyethene 2 are totally complementary: 1 and 2 exclusively form the 2, 2-diethoxyoxetane 4 in polar solvents at room temperature. Contrary to the literature this thermal cycloadditon proceeds uncatalyzed. 1 and 2 react photochemically under exclusive formation of the regioisomer oxetane 3-preferably in nonpolar solvents. The inversion (“Umpolung”) of the reactivity of ...