The synthesis of the 8-phosphabicyclo[3.2.1]octanic system

Y. Kashman, O. Awerbouch

Research output: Contribution to journalArticlepeer-review


The 8-phosphabicyclo[3.2.1]octanic system was synthesized in two different ways: (a) a double Michael addition ofaryl phosphine to 2,6-cycloheptadienone (b) a Diels-Alder cycloaddition of dichlorophenylphosphine to 3,5-cycloheptadienyl-1-acetate. The stereochemistry of the isomeric phosphines (I, II and IX) was determined by investigation of the NMR spectra of their derivatives (oxides, ketals, benzyl phosphonium salts and the uranyl nitrate complexes of the oxides and the ketals). The conformations of several compounds are discussed, as well as the hydrolysis mechanism of two benzyl phosphonium salts which gave a mixture of products.

Original languageEnglish
Pages (from-to)4213-4225
Number of pages13
Issue number17
StatePublished - 1970


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