Synthesis and reactions of 5-methylenebicyclo [2.2. 0] hex-2-ene derivatives from hexamethyl (Dewar benzene)

CC Wamser, DD Ngo, MJ Rodriguez…

Index: Wamser, Carl C.; Ngo, David D.; Rodriguez, Michael J.; Shama, Sami A.; Tran, Thuan L. Journal of the American Chemical Society, 1989 , vol. 111, # 6 p. 2162 - 2168

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Citation Number: 2

Abstract

Abstract: Treatment of hexamethyl (Dewar benzene)(HMDB) with tert-butyl hypochlorite provides a rearranged chlorinated derivative, exo-6-chloro-l, 2, 3, 4, 6-pentamethyl-5- methylenebicyclo [2.2. 0] hex-2-ene (1). Thermal rearrangement of 1 gives pentamethylbenzyl chloride (4); the activation energy decreases in more polar solvents, suggesting an ionic intermediate during the chloride migration and/or ring opening. The ...