The toluene-p-sulphonates (I) and (II) of erythroxylol B and its saturated analogue have been solvolysed in buffered acetic acid. Each leads to approximately equal amounts of two bridgehead acetates, (III) and (IV) from (I), (XIII), and (XIV) from (II). The rate of solvolysis of (II) is twelve times greater than that of neophentyl tosylate at 100°.
J. C. Fairlie, R. McCrindle and R. D. H. Murray, J. Chem. Soc. C, 1969, 2115 DOI: 10.1039/J39690002115
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