3727-48-8

Usage

Structure

Substituted cyclohexadiene derivative with a bromine atom attached to the second carbon of the cyclohexadiene ring

Applications

a. Organic synthesis
b. Building block in the synthesis of more complex organic compounds
c. Intermediate in the pharmaceutical and agrochemical industries
d. Potential applications in material science
e. Reagent in chemical research

Chemical reactions

Can undergo substitution, addition, and elimination reactions

Safety

Handle with care due to potential hazards if not properly managed

Upstream product

• 17202-32-3 1,6-dibromocyclohex-1-ene 
• 14310-04-4 2-bromocyclohex-2-en-1-yl acetate 
• 97861-71-7 2-bromo-2-cyclohexenyl diethyl phosphate 
• 2568-36-7 6,6-dibromobicylo[3.1.0]hexane 
• 109380-07-6 2-bromocyclohex-2-en-1-ol 
• 97861-66-0 ethyl 2-bromo-2-cyclohexenyl carbonate 

Downstream Products

• 211503-84-3 2-chloro-5-(1,5-cyclohexadienyl)pyridine 
• 1233405-12-3 (E)-2-(2-(tert-butyldimethylsilyloxy)-5,5-dimethylcyclohexylidene)-1-(cyclohexa-1,5-dienyl)ethanone 
• 84099-68-3 1-(1,3-cyclohexadiene-2-yl)-1-methoxy-1-cyclopropylmethanol 
• 211503-87-6 (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 211503-90-1 (1S,4R,5R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]octane-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 211503-92-3 N-[(1R,2R,4R)-4-bromo-2-(6-chloro(3-pyridyl))cyclohexyl](tert-butoxy)carboxamide 
• 211503-91-2 (-)-tert-butyl N-[(1R,2R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohexyl]carbamate 
• 217323-82-5 (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine 
• 140111-52-0 epibatidine 
• 84099-61-6 1,5-Cyclohexadiene-1-carboxaldehyde 

Relevant academic research and scientific papers

Simple and efficient synthesis of bromine-substituted 1,3-dienes and 1,3,5-cycloheptatriene by vacuum pyrolysis of gem-dibromocyclopropanes

To establish whether the results obtained by the gas phase pyrolysis of 6,6-dihalobicyclo[3.1.0]hexanes by HeI photoelectron spectroscopy using a high power CW CO2 laser as a directed heat source can be achieved on a preparatory scale using a modified apparatus, we carried out the gas phase pyrolysis of a few representative gem-dibromocyclopropanes such as 1,1-dibromo-2,2,3,3-tetramethylcyclopropane (1), 1,1-dibromo-2,2-dimethyl-cyclopropane (2), 1,1-dibromo-cis-2,3-dimethylcyclopropane (3), 1,1-dibromo-trans-2,3-dimethylcyclopropane (4), 6,6-dibromobicyclo[3.1.0]hexane (5) and 7,7-dibromobicyclo[4.1.0]heptane (6). Except 7,7-dibromobicyclo[4.1.0]heptane, that gave 1,3,5-cycloheptatriene in 72% yield at 525°C, 1, 2, 3, 4 and 5 readily lose HBr at 400-560°C in the gas phase to produce β-bromo-1,3-dienes in high chemical yields and purity. The dienes are potentially useful starting substrates for the Diels-Alder reactions.

Chemoselectivity in Palladium-Catalyzed Reactions of 2-Bromoallyl Esters

The chemoselectivity of palladium-catalyzed reactions of 2-bromoallyl esters has been established.With compatible carbon nucleophiles, 2-bromoallyl esters gave products of couplling to the vinyl bromide moiety instead of nucleophilic allylic substitution.Products from reactions with nitrogen nucleophiles and in the absence of added nucleophiles are also consistent with the absence or minor importance of the (?-allyl)palladium complex formation as a competing pathway.These results illustrate an unusual influence of the 2-bromo substituent on the usual ease of fission of the allylic C-O bond.

A NEW TYPE OF FUNCTIONAL GROUP DIFFERENTIATION IN PALLADIUM-CATALYZED REACTIONS

Products of palladium-catalyzed ethynylations of various 2-bromoallyl acetates show that the formation of ?-vinylpalladium intermediates, instead of ?-allylpalladium complexes, is preferred in such substrates.

PRACTICAL METHOD FOR USING ALKOXIDE-ACCELERATED VINYLCYCLOBUTANE RING EXPANSIONS IN THE SYNTHESIS OF SIX-MEMBERED RINGS. UNEXPECTED ORBITAL SYMMETRY ALLOWED AND FORBIDDEN 1,3-SIGMATROPIC REARRANGEMENTS.

A practical method for utilizing the ring expansion of 2-vinylcyclobutanols to cyclohex-3-en-1-ols, even in cases in which very acid-sensitive groups are present, consists of the addition of 1-lithio- 1-methoxycyclopropanes to conjucated enals, brief trea