Journal of the American Chemical Society

Stepwise and concerted solvolytic elimination and substitution reactions: E1 reaction via a primary carbocation

Q Meng, A Thibblin

Index: Meng, Qingshui; Thibblin, Alf Journal of the American Chemical Society, 1997 , vol. 119, # 21 p. 4834 - 4840

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Citation Number: 16

Abstract

Solvolysis of 9-(X-methyl) fluorene (1-X, X= I, Br, OBs) in 25 vol% acetonitrile in water gives the elimination product 9-methylidenefluorene and the substitution products 9- (hydroxymethyl) fluorene (1-OH) and 9-(acetamidomethyl) fluorene (1-NHCOMe). Kinetic studies of the corresponding ring-substituted compounds 2-X and 3-X show that the rate of elimination increases with increasing acidity of the substrate, Brønsted α> 0. The small ...