Journal of Organic Chemistry p. 900 - 906 (1980)
Update date:2022-08-05
Topics:
Traynor, Sean G.
Kane, Bernard J.
Coleman, Jacquelyn B.
Cardenas, Carlos G.
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.
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