Since certain a-dialkylaminomethyl-2 or 4-chloro-l-naphthalenemethanols(1, 2, 3, 4) possessed considerable antimalarial activity, it was desirable to study the effect of further varying the position of the halogen. This paper reports the
trum of the higher melting racemate. We assigned the downfield doublet to the proton on Ci and the central multiplet to the overlapping resonances of the two neighboring protons on Ca and C3. These selections were based on a comparison with the nmr spectrum of 1,1,2,3,3pentaphenyl-1-propanol, which shows only two absorptions apart from the phenyl multiplets. The hydroxyl proton of the latter was identified by deuterium exchange, leaving the Ca and C3 protons with overlapping resonances.The 132°C melting compound reported by earlier workers (7, 4) is undoubtedly a mixture of diastereomers. The acetonate of Kohler, mp 160-161 °C, is the acetonate of our higher melting racemate. The available data do not permit the assignment of absolute configurations.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.