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β-Elimination of 9-(Methoxy)Methylfluorene in Methanolic Sodium Methoxide

R. A. More O'Ferrall and P. J. Warren
Proceedings of the Royal Irish Academy. Section B: Biological, Geological, and Chemical Science
Vol. 77 (1977), pp. 513-521
Published by: Royal Irish Academy
Stable URL: http://www.jstor.org/stable/20494316
Page Count: 9
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β-Elimination of 9-(Methoxy)Methylfluorene in Methanolic Sodium Methoxide
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Abstract

β-Elimination of 9-(methoxymethyl)fluorene in CH₃OD and of the 9-deuteriated substrate in CH₃OH are subject to kinetic induction periods similar to those observed with the corresponding 9-(hydroxymethyl)fluorene arising from competing hydrogen isotope exchange between substrate and solvent. A kinetic analysis in which rate constants for a series first order kinetic scheme are evaluated iteratively shows the mechanism of elimination to be ElcB. Despite the twenty times greater reactivity of the methoxy than hydroxy leaving group, enhancement of the small component of E2 elimination thought to accompany the predominantly ElcB pathway for the 9-(hydroxymethyl)fluorene is not observed. The unexpectedly higher rate of ionisation of the 9-fluorenyl hydrogen in 9-methoxymethyl than 9-(hyroxymethyl)fluorene is compared with behaviour in related systems.

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