Regioselective ring opening in substituted benzocyclopropenes. An alternative or complementary mechanism for electrophilic substitution involving attack at. alpha. …

LK Bee, PJ Garratt, MM Mansuri

Index: Bee, Lim Keow; Garratt, Peter J.; Mansuri, Muzamil M. Journal of the American Chemical Society, 1980 , vol. 102, # 23 p. 7076 - 7079

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Citation Number: 27

Abstract

Abstract: 2-Methylbenzocyclopropene (5) reacts with bromine, iodine, and HCl to give the m- xylenes 12a, c, d as the major products, whereas it reacts with silver nitrate in the presence of ethanol and aniline to give the o-xylenes lle, f as the major products. Similarly, 3- methylbenzocyclopropene (10) gives mainly m-xylenes 14a, c, d with halogens and HC1 and gives p-xylenes 13e, f with silver nitrate and ethanol or aniline. Cyclopropa [3, 4] ...