Hydrogen–deuterium exchange of medium ring cycloalkenes during deuterogenation with tris(triphenylphosphine)chlororhodium(I)

Publisher Website
Google Scholar
Abstract
Cyclooctene, and, to a lesser extent, cycloheptene and cyclododecene undergo H–D scrambling during deuterogenation with tris(triphenylphosphine)chlororhodium(I), whereas this catalyst affords clean addition of two deuterium atoms to cyclohexene and 1-octene. Cyclooctene containing up to 0.4 deuterium atoms per molecule has been isolated after 50% reduction and the isotope shown to be randomly distributed about the ring. This unexpected exchange reaction has been accounted for in terms of the medium size ring effect (I-strain) and provides impressive further evidence for the reversible formation of a normally unobserved rhodium–alkyl species as an intermediate in the hydrogenation reaction.

This publication has 0 references indexed in Scilit: