Abstract
Catalytic deuteriation of cycloalkenes using [RhX(PR3)3](X = halide, R = aryl) catalysts frequently gives rise to some polydeuteriation and scrambled addition of deuterium to the cycloalkene substratrate. It is shown that these undesirable side reactions can be minimized by using small, electronegative aniono ligands or electron-withdrawing triarylphosphine ligands. Both these ligands inhibit the decomposition of the 16-electron intermediate rhodium(III) alkyl complex [RhD(X)(alkyl)(PR3)2]. Its decomposition by β-hydride abstraction brings about both polydeuteriation and scrambled addition of deuterium to the alkene. Acyclic, alk-1-enes give the best yields of [2H2] products when [Rhl(PPh3)3] is the catalyst, since the formation of the less stable 2-alkyl intermediate is sterically inhibited.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
