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

Y. Kashman, O. Awerbouch

Research output: Contribution to journalArticlepeer-review

Abstract

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
JournalTetrahedron
Volume26
Issue number17
DOIs
StatePublished - 1970

Fingerprint

Dive into the research topics of 'The synthesis of the 8-phosphabicyclo[3.2.1]octanic system'. Together they form a unique fingerprint.

Cite this