The Journal of Organic Chemistry

Photocyclization of stilbenes. VII. Unusual fluorine atom rearrangement in the photocyclization of 1-fluoro [5] helicenes

FB Mallory, CW Mallory

Index: Mallory, Frank B.; Mallory, Clelia W. Journal of Organic Chemistry, 1983 , vol. 48, # 4 p. 526 - 532

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Citation Number: 21

Abstract

Oxidative photocyclization of l-fluoro [5] helicene and two of its chlorine-substituted derivatives leads to the formation of 8-fluorobenzo [ghi] perylenes through an unprecedented inter-ring fluorine atom migration; photoelimination of HF to give benzo [ghi] perylenes also occurs as a competing process. The rearrangement pathway predominates when the irradiation is carried out at 0" C in air-saturated benzene solution containing M ...