28627-52-3

Upstream product

• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 62-53-3 aniline 
• 76-22-2 Camphor 
• 1191099-59-8 (1R,4R)-1-oxo-2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)-hydrazinium-1-olate 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 10293-06-8 (1R)-3-endo-bromocamphor 
• 76-29-9 3-bromocamphor 
• 100-61-8 N-methylaniline 
• 3282-99-3 1,1-bis-(4-aminophenyl)cyclohexane 
• 138966-59-3 1,1-bis-(4-amino-phenyl)-3-methyl-cyclohexane 
• 911850-12-9 (1R,4R)-1,7,7-trimethyl-2-(phenylamino)bicyclo[2.2.1]heptane-2-carbonitrile 

Downstream Products

• 911850-13-0 (5S,8R)-3-butyl-5,6,7,8-tetrahydro-4-hydroxy-8,9,9-trimethyl-1-phenyl-5,8-methanoquinolin-2(1H)-one 
• 16560-40-0 (+/-)-4-hydroxy-7,11,11-trimethyl-6-phenyl-7,8,9,10-tetrahydro-7,10-methano-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione 
• 720672-58-2 rac-3-butyl-4-hydroxy-8,9,9-trimethyl-1-phenyl-5,6,7,8-tetrahydro-5,8-methanoquinolin-2(1H)-one 
• 508-32-7 tricyclene 
• 5794-04-7 camphene 
• 759457-76-6 N-isobornylaniline 
• 75946-22-4 N-bornylaniline 
• 118759-88-9 N-isobornyl aniline 
• 118693-56-4 N-isobornyl-N-methylaniline 
• 485319-27-5 (5S,8R)-3-bromo-3-butyl-8,9,9-trimethyl-1-phenyl-5,6,7,8-tetrahydro-5,8-methanoquinoline-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Debromination of endo-(+)-3-bromocamphor with primary amines

Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.

Reaction of malonates with camphoranile synthesis of 4-hydroxy-2-pyridones attached to the bornane ring system

The reaction of camphoraniles 3a,b with "magic malonates" (bis-2,4,6-trichlorophenylmalonates) 4a,b leads to 4-hydroxy-2(1H)-pyridones attached to bornane ring system 6a-c in good yields. Less satisfactory yields were obtained with the diethyl malonate 5b

Nickel complex catalyzed reduction of imines

The 1:1 complexes formed in situ from nickel(II) acetate and the thiosemicarbazones of ortho-hydroxy aromatic aldehydes catalyze the hydrosilylation of imines. A variety of imines were reduced in good to excellent yields employing two equivalents of a silane such as triethylsilane and 5 mol% of the catalysts.

SYNTHESIS OF AMINES BY REDUCTION OF IMINES WITH THE MCl2/NaBH4 (M = Co, Ni) SYSTEM

A simple method for the synthesis of amines by the reduction of imines, anils and enamines, including some chiral substrates, with the MCl2/NaBH4/CH3OH reagent (M = Co, Ni) in 64-82percent yield is described.

Amines as Dehalogenating Agents. IV. Hydrocarbons, N-Bornyl- and N-Isobornylaniline Formation in the Reaction between 3-Bromocamphor and N-Methylaniline

N-Methylanilin (4) reagiert bei 200 deg C im Vergleich zu N,N-Dimethylanilin entweder mit 3-Bromcamphor (2) oder Camphor (3) zu den Kohlenwasserstoffen, Camphen 5 und Tricyclen 6 und N-Bornylanilin (exo-endo-Isomers 7).Bei der Reaktion mit 3 ist Saeurekatalyse notwenig.Untersuchungen zum Mechanismus erlauben es, anzunehmen, dass Camphoranil 8 ein gemeinsames Zwischenprodukt fuer alle Produkte und 4 der H-Donator in den Reduktionsstufen ist, auf der Grundlage von kinetischen und stereochemischen Beweisen und unabhaengigen chemischen Experimenten.