A fractional loss of 90% of one deuterium in the formation of deuterionorticyclene-1-carboxylic acid methyl ester (4a) on solvolysis of endo,endo-5,6-dideuterio-exo-2-bromonorbornane-1-carboxylic acid methyl ester (1b) is consistent with at least a 15 : 1 preference for cleavage of an endo- over exo-C–H bond at C-6.
N. H. Werstiuk, J. Chem. Soc. D, 1970, 1499b DOI: 10.1039/C2970001499B
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