Photoinduced electron-transfer reactions. Radical cations of methylenebicyclo [2.2. 0] hexene derivatives
…, MLM Schilling, CC Wamser
Index: Roth, Heinz D.; Schilling, Marcia L. Manion; Wamser, Carl C. Journal of the American Chemical Society, 1984 , vol. 106, # 17 p. 5023 - 5025
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Citation Number: 19
Abstract
The reaction of 6-chloro-5-methylene-1, 2, 3, 4, 6-~ entamethylbicyclo [2.2. 0] hex-2-ene (la, R= C1) with photoexcited chloranil in acetone generates pentamethylbenzyl chloride (6a) efficiently, The formation of this product requires the opening of the transannular bond and a 1, 3-(or 1, 7-) chlorine migration. During this reaction, pronounced CIDNP effects are observed (Figure 1, upper), which allow an insight into the reaction mechanism. The ...
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