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The deoxydehydration of carbohydrates represents a key target to leverage renewable biomass resources chemically. Using a vanadium(V)‐based catalyst, it was possible to directly deoxydehydrate cyclic  trans ‐diol substrates. Accompanying mechanistic characterisation of this process by density functional calculations pointed to an energetically tractable route for deoxydehydration of cyclic  trans ‐diol substrates involving stepwise cleavage of the diol C−O bonds via the triplet state; experimentally, this was supported by light dependence of the reaction. Calculations also indicated that cyclic  cis ‐diols and a linear diol substrate could additionally proceed by a concerted singlet DODH mechanism. This work potentially opens a new and cost‐effective way to efficiently convert carbohydrates of  trans ‐diol stereochemistry into alkenes.

chemsuschem

Direct Deoxydehydration of Cyclic  trans ‐Diol Substrates: An Experimental and Computational Study of the Reaction Mechanism of Vanadium(V)‐based Catalysis **