The Uncatalyzed addition of acetic acid to norbornadiene

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Title: The Uncatalyzed addition of acetic acid to norbornadiene
Author: Cristol, Stanley; Morrill, Terence; Sanchez, Robert
Abstract: The uncatalyzed addition of acetic acid to norbornadiene (I) to give mixtures of ezo-dehydronorbornyl acetate (II) and nortricyclyl acetate (III) was studied. Rates of addition and ratios of II/III (degree of homoallylic rearrangement) were found to be quite sensitive to solvent changes. Addition of acetic acid-O-dl permitted a study of the stereochemistry of addition and a measure of the accompanying Wagner-Meerwein rearrangement. An examimtion of the relationship between homoallylic and Wagner-Meerwein rearrangements has been made.
Record URI: http://hdl.handle.net/1850/2133
Publishers URL: http://dx.doi.org/10.1021/jo01347a003
Date: 1966-09-12

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