2430-60-6

Upstream product

• 670-54-2 ethenetetracarbonitrile 
• 73073-31-1 2>-1,2-Dihydronaphthalin 
• 73073-31-1 2>-1,2-Dihydronaphthalin 
• 447-53-0 1,2-Dihydronaphthalene 
• 99796-89-1 <1,1,2,2-D4>-1,2-dihydronaphthalene 
• 103-26-4 methyl cinnamate 

Relevant academic research and scientific papers

Hydrogen Transfer Reactions, 7. Regio- and Stereoselectivity in the Dehydrogenation Steps during Homogeneously Catalysed Hydrogen Transfer

In the disproportionation of 1,2-dihydronaphthalene catalysed by metal complexes, especially by the Wilkinson catalyst (7), the elimination occurs in two steps.The abstraction of the first hydrogen proceeds with but a small preference for the 2-position - in contrast to dehydrogenations via hydride transfer.The second hydrogen is removed highly stereospecifically from the vicinal cis-position, the acceptor being cis-hydrogenated.Intermolecular H/D-scrambling may occur via allyl hydrido complexes.

Hydrogen Transfer Reactions, 6. Dehydrogenation of 1,2-Dihydroarenes by Quinones: Regio- and Stereoselectivity in the Two-Step Mechanism

1,2-Dihydronaphthalene (1) is dehydrogenated by o- and p-quinones in a two-step mechanism.In the rate determining step a hydride ion is abstracted from the 2-position by o-chloro- (4a) and o-bromoanil (4b) with high regioselectivity.Ion pairing leads to highly stereoselective cis-elimination of the proton.Stereoselectivity, primary isotope effects, and activation entropy are consistent with a coplanar coordination in the transition state and participation of tunneling. p-Quinones show different regioselectivity in the hydride abstraction step.The dehydrogenation of 9,10-dihydrophenanthrene (3) proceeds in a similar way.

Hydrogen transfer Reactions, Part 4. Mechanism in the Stereoselective Hydrogen Transfer from 1,2-Dihydronaphthalene to Tetracyanoethene

The hydrogen transfer between 1,2-dihydronaphthalene (1) and tetracyanoethene (2) is highly stereoselective.Kinetic isotope effects exclude an electrocyclic reaction and support an ionic multistep mechanism.Stereoselectivity is caused by steric fixation in the intermediate ion pair.

Hydrogen Transfer Reactions, Part 2. Radical Mechanism of Thermal Disproportionation of 1,2-Dihydronaphthalene

In the thermal disproportionation of 1,2-dihydronaphthalene (1) both hydrogen abstraction and addition are stereo-unspecific radical reactions.An electrocyclic mechanism was excluded.