New light is thrown on the reactivity of the reagents DBU and DBN, which are often used in base-induced dehydrohalogenations, by their reaction with chloro- and dichlorophosphanes. They form chloride salts with onio- and dionio-substituted phosphanes as cations; that is, DBN and DBU behave as nucleophiles! After anion exchange with KPF6 these salts can be obtained in crystalline form. The dication 1, for example, was characterized by X-ray diffraction. R = (cyclo-C6H11)2N.
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Reed et al. (1993) studied this question.
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