Rearrangement of an exchangeable hydrogen during the reduction of maleimide with lithium aluminum hydride

Tethered bis‐2,5‐dimethylene‐2,5‐dihydrofurans were generated in the gas phase by flash vacuum pyrolysis (FVP) of diester precursors. These furan‐based bis(p‐quinodimethanes) are shown to undergo reactions leading to macrocycles. The observed products strongly support a mechanism involving cyclic diradical intermediates. Formation of the furan‐based p‐quinodimethane and the corresponding cyclization chemistry was studied by high‐level ab initio calculations. The theoretical studies reveal the importance of the entropy‐driven elimination steps in the high‐temperature FVP chemistry.

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The chemistry of thiophene-based bis-(p-quinodimethanes): an approach to macrocycles

Trahanovsky

Klumpp

2016

Tetrahedron Letters

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Rearrangement of an exchangeable hydrogen during the reduction of maleimide with lithium aluminum hydride

Cited by 11 publications

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ChemInform Abstract: REARRANGEMENT OF AN EXCHANGEABLE HYDROGEN DURING THE REDUCTION OF MALEIMIDE WITH LITHIUM ALUMINUM HYDRIDE

ChemInform Abstract: REARRANGEMENT OF AN EXCHANGEABLE HYDROGEN DURING THE REDUCTION OF MALEIMIDE WITH LITHIUM ALUMINUM HYDRIDE

Intramolecular Reactions of Tethered Furan‐Based Bis(p‐quinodimethanes)

The chemistry of thiophene-based bis-(p-quinodimethanes): an approach to macrocycles

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