Solvent dependence of singlet oxygen/substrate interactions in ene-reactions,(4+ 2)-and (2+ 2)-cycloaddition reactions

K Gollnick, A Griesbeck

Index: Gollnick, Klaus; Griesbeck, Axel Tetrahedron Letters, 1984 , vol. 25, # 7 p. 725 - 728

Full Text: HTML

Citation Number: 44

Abstract

Abstract Product formation of singlet oxygen reactions with simple olefins occurring as ene- reactions,(4+ 2)-and (2+ 2)-cycloaddition reactions is independent on solvent polarity. Thus, 2, 3-dimethyl-2-butene (1) and 2-methy]-2-butene (3), 1, 3-cyclohexadiene (6), and benzvalene (8) yield allylic hydroperoxides (2) and (4)(54%)+(5)(46%), endoperoxide (7), and dioxetane (9), respectively. The rates of the ene-reactions and (4+ 2)-cycloaddition ...