Abstract
We found that this bond is also cleaved with 4-hydroxy-3,5-di-tert-butylbenzylidene chloride I. Reactions of I with aminals II occur with a heat release upon mixing the reactants (neat or in solvents such as ether or hexane). Irrespective of the structure of the aminal and reactant ratio, gem-dichloride I undergoes dehydrochlorination and dechloroamination with the formation of 4-(dialkylaminoor piperidino)methylene-3,5-di-tert-butylcyclohexa-2,5-dienones III. The dialkylamine formed in the dehydrochlorination step, as found in additional experiments, further reacts with I to form salt V [3, 4]. When the reaction of I with IIa was performed in diethyl ether, a crystalline mass consisting of IVa and Va was obtained. By its treatment with ethyl diphenylphosphinite, we obtained individual products: (dimethylamino)methyldiphenylphosphine oxide VI and dimethylammonium chloride Va.
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