80394-98-5

Upstream product

• 201230-82-2 carbon monoxide 
• 56914-94-4 8-exo-chloro-exo-tetrahydrodicyclopentadiene 
• 15904-95-7 exo-Tricyclo<5.2.1.0^2,6>decanol-(8) 

Downstream Products

• 2825-83-4 (3aR,4S,7R,7aS)-Octahydro-4,7-methano-indene 
• 93107-41-6 α-cyano-m-phenoxybenzyl exo-tricyclo<5.2.1.0^2,6>decane-endo-2-carboxylate 
• 109430-44-6 5-benzylfur-3-ylmethyl exo-tricyclo<5.2.1.0^2,6>decane-endo-2-carboxylate 
• 93107-48-3 2-methyl-3-allyl-4-oxocyclopent-2-enyl exo-tricyclo<5.2.1.0^2,6>decane-endo-2-carboxylate 
• 80623-06-9 exo-Tricyclo<5.2.1.0^2,6>decan-endo-carbonsaeure-(2)-chlorid 

Relevant academic research and scientific papers

Isomerisation Reactions of Dicyclopentadiene Derivatives. Preparation of Amides and Carboxylic Acids

The dicyclopentadiene (DPD) derivatives 8,9-endo-dihydro-DPD (1), 8-exo-hydroxy-exo-tetrahydro-DPD (2) and 2-hydroxy-endo-tetrahydro-DPD (3) have been reacted with acetonitrile in sulfuric acid. Reaction for 6 h at 30 deg C gave an 82percent yield of N-(2-exo-tetrahydro-DPD-yl)acetamide (5a). Reaction of 3 for 1 min at 20 deg C gave N-(2-endo-tetrahydro-DPD-yl)acetamide (4a, 95percent yield) and reaction of 2 with acetonitrile and boron trifluoride in sulfur dioxide gave a 95percent yield of N-(exo-8-exo-tetrahydro-DPD-yl)acetamide (6a). The reactions of 3 with benzonitrile and substituted benzonitriles were monitored by 1H NMR spectroscopy. The observed rate constants could be correlated by the Hammett ?- constants with a ρ constant of 1.00 (R2 = 0.987). These results were in accordance with a reaction scheme in which the isomerisations proceed via carbocations in equilibria with nitrile adducts. Reaction of 8-exo-chloro-exo-tetrahydro-DPD (13) with carbon monoxide and antimony pentafluoride in sulfur dioxide gave 2-carboxy-endo-tetrahydro-DPD (15) at -78 deg C and 2-carboxy-exo-2-tetrahydro-DPD (17) at 20 deg C.