Interactions of singlet oxygen with 2, 5-dimethyl-2, 4-hexadiene in polar ano non-polar solvents evidence for a vinylog ene-reaction

K Gollnick, A Griesbeck

Index: Gollnick, Klaus; Griesbeck, Axel Tetrahedron, 1984 , vol. 40, # 17 p. 3235 - 3250

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Citation Number: 31

Abstract

2, 5-Dimethyl-2, 4-hexadiene (1) was studied as a singlet oxygen acceptor in various solvents. 1 undergoes concomitantly the three well-known modes of singlet oxygen reactions:(1) the ene-reaction to give the allylic hydroperoxide 3,(2) the (4+ 2)-cycloaddition to give the endoperoxide 4, and (3) the (2+ 2)-cycloaddition to give the dioxetane 2. Beyond that (and in contrast to simple olefins), there are (4)“physical” quenching and (5) a “vinylog ...