Mechanistic insights into the rhenium-catalyzed alcohol-to-olefin dehydration reaction.
Rhenium-based complexes are powerful catalysts for the dehydration of various alcohols to the corresponding olefins. Here, we report on both experimental and theoretical (DFT) studies into the mechanism of the rhenium-catalyzed dehydration of alcohols to olefins in general, and the methyltrioxorhenium-catalyzed dehydration of 1-phenylethanol to styrene in particular. The experimental and theoretical studies are in good agreement, both showing the involvement of several proton transfers, and of a carbenium ion intermediate in the catalytic cycle.
Organic Chemistry & Catalysis, Debye Institute for Nanomaterials Science, Faculty of Science, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht (The Netherlands), Fax: (+31) 30-252-3615.
Ties J
TJ
Korstanje
Johann T B H
JT
Jastrzebski
Robertus J M
RJ
Klein Gebbink
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D003681:Dehydration; D009942:Organometallic Compounds / Q000737:chemistry*; D011522:Protons; D011789:Quantum Theory; D012211:Rhenium / Q000737:chemistry*
D000438:Alcohols; D000475:Alkenes; D056831:Coordination Complexes; D009942:Organometallic Compounds; D011522:Protons; D012211:Rhenium; C411866:methyltrioxorhenium VII
alcohols; dehydration reaction; density functional calculations; reaction mechanisms; rhenium