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Treatment of ethyl 4-bromobutylphosphonochloridate with phenylmagnesium bromide, followed by acid-catalysed hydrolysis of the product, gave 4- bromobutyl(phenyl)phosphinic acid. This was converted into the corresponding phosphinamide by treatment with thionyl chloride and then with aqueous ammonia. Cyclodehydrobromination with sodium hydride in warm xylene then gave a good yield of 2-phenylperhydro-1,2- azaphosphorine 2-oxide. Some other routes to this compound were investigated.

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Chlorination of 2,4-, 2,6- and 3,5-di-t-butylphenols gave the chlorocyclohexa-dienones (2a), (10), and (7) and (9), respectively. Base-catalysed methanolysis of the ketones (2a) and (9) produced the rearranged gem-dimethoxycyclohexadienones (5)and (11). Under similar conditions the ketone (7) rearranged to 3,5-di-t-butyl-2,4- dichlorophenol, while (10) was converted into a mixture of 2,6-di-t-butyl-1,4-benzo-quinone and 3,5,3',5'-tetra-t-butyl-4,4'-diphenoquinone. The dibromocyclohexa-dienone (2b) also dimerized in the presence of base, affording a low yield of 2,2'-dihydroxy-3,5,3',5'-tetra-t-butylbiphenyl. The mechanisms of these reactions are discussed.

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