32139-60-9

Upstream product

• 74697-30-6 (1S,6R,7S)-7-Methyl-7-(1-methyl-cycloprop-2-enyl)-2,5-diphenyl-3,4-diaza-bicyclo[4.1.0]hepta-2,4-diene 
• 6830-78-0 3,6-diphenyl-1,2,4,5-tetrazine 
• 31707-64-9 1,1'-Dimethylbi-2-cyclopropen-1-yl 
• 74697-30-6 7-methyl-7-(1-methylcycloprop-2-enyl)-2,5-diphenyl-3,4-diazabicyclo[4.1.0]hepta-2,4-diene 
• 108-86-1 bromobenzene 
• 53731-21-8 1,5-Dimethylbicyclo<3.3.0>octane-3,7-dione 

Relevant academic research and scientific papers

An one-pot synthesis of semibullvalenes and its mechanism

1,2,4,5-Tetrazines 7 readily react with 3,3′-bicyclopropenyl 8 in a cycloaddition-cycloelimination sequence to give 3,4-diazanorcaradienes 9 with endo configuration of the methyl group at C-7. On gentle heating in inert solvents, these 3,4diazanorcaradienes 9 are cleanly transformed into semibullvalenes 11. This reaction sequence can also be performed as a one-pot method. Kinetic investigations and comparisons with two model systems are in agreement with the proposed reaction mechanism.

ZUM MECHANISMUS DER SEMIBULLVALEN-BILDUNG AUS 1,2,4,5-TETRAZINEN UND BIFUNKTIONELLEN CYCLOPROPENEN

A mechanism is proposed for the multi-step reaction of 1,2,4,5-tetrazines 1 and the bifunctional cyclopropene 2a to form substituted semibullvalenes 8.

Cycloaddition von N-phenyltriazolindion an 1,5-dialkyl substituierte semibullvalene

Starting from bicyclo[3.3.0]octa-3,7-diones, several 3- and 7-substituted semibullvalenes were prepared. Cycloaddition of N-phenyltriazolindione to some of these semibullvalenes lead with rearrangement of the carbon skeleton to dihydrodiazatriquinacenes.