Chemistry of the 2-Pinanols. 2. Investigation of the Utility of the Enhanced Basicities of the Pinanoxide Bases

Article abstract of DOI:10.1021/jo01293a026

The utility of the alkoxides of cis- and trans-2-pinanol has been investigated.Yiels comparable to and exceeding those obtained with tert-butoxide are reported for the alkylation of ethyl acetoacetate, for the conversion of α-pinene oxide to trans-pinocarveol and cis-3-pinen-2-ol, and for the isomerization of vinylnorbornene and limonene.Dehydrohalogenation was effected rapidly on bornyl chloride and 2,6-dichlorocamphane-compounds reported to be inert to potassium tert-butoxide in tert-butyl alcohol.Reactions with 1-octyl bromide and with benzyl chloride showed that the pinanoxides have nucleophilicities comparable to that of tert-butoxide.