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Decarbonylation dehydration of fatty acids to alkenes in the presence of transition metal complexes

1976; Wiley; Volume: 53; Issue: 12 Linguagem: Inglês

10.1007/bf02635473

1558-9331

Thomas A. Foglia, P. A. Barr,

Synthetic Organic Chemistry Methods

Abstract The catalytic decarbonylation of stearic acid into a mixture of heptadecenes has been accomplished by use of a catalyst system comprised of rhodium trichloride (RhCl 3 ) and triphenylphosphine. The isomeric composition of the heptadecenes formed was found, by spectroscopic and chemical methods, to be dependent upon the type of rhodium catalyst employed. Anhydrous RhCl 3 produced about the same amount of 2‐heptadecene, twice the amount of 3‐heptadecene, and about half the amount of 1‐heptadecene as hydrated RhCl 3 . The active catalytic species formed in situ has been identified as the rhodium I complex [(C 6 H 5 ) 3 P] 2 Rh(CO)Cl. A mechanistic pathway to account for the observed decarbonylation products employing the above catalyst is presented.