13237-88-2

Usage

Uses

Used in Chemical Synthesis:
Bicyclo[2.2.1]heptane,7-bromois used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure and reactivity make it a valuable building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Synthesis of Methyl Norbornane-7-carboxylate:
Specifically, 7-Bromobicyclo[2.2.1]heptane has been utilized in the synthesis of methyl norbornane-7-carboxylate, a compound with potential applications in various industries. The synthesis of Bicyclo[2.2.1]heptane,7-bromo- involves the reaction of 7-Bromonorbornane with other reagents, resulting in the formation of the desired product. This process highlights the versatility and utility of Bicyclo[2.2.1]heptane,7-bromoas a synthetic intermediate in the chemical industry.

InChI:InChI=1/C7H11Br/c8-7-5-1-2-6(7)4-3-5/h5-7H,1-4H2

Upstream product

• 22365-94-2 anti-C₇H₉Br 
• 56263-62-8 Bicyclo[2.2.1]heptane-7-carboperoxoic acid tert-butyl ester 
• 70279-05-9 7-iodonorbornane 
• 51689-30-6 7,7-dibromoborbornane 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 5971-67-5 bicyclo<2.2.1>heptane-7-carboxylic acid 
• 5971-67-5 7-carboxybicyclo<2.2.1>heptane 
• 374729-47-2 (C₆H₁₀CC(C₆H₂(OH)2C(CH₃)3)2) 
• 219948-09-1 bis(5-tert-butyl-3,4-dimethyxyphenyl)methylenenorbornane 
• 219948-08-0 bis(5-tert-butyl-3,4-dimethyxyphenyl)norbornyl carbinol 
• 219948-10-4 bis(5-tert-butyl-3,4-benzoquinonyl)methylenenorbornane 

Relevant academic research and scientific papers

Oxidative coupling of 7,7-dilithionorbornane; 7,7′-dilithio-7,7′-dinorbornyl, a new vic-dilithioalkane prone to a new mode of decomposition

7,7-Dilithionorbornane reacts with butyl halides at -100°C to give 7,7′-dilithio-7,7′-dinorbornyl (30%), which is easily oxidized to 7,7′-dinorbornylidene.

Reactions of Some Bicycloalkyl Iodides with Bromine

The reactions of normally unreactive bicyclic iodides such as 1- and 7-iodonorbornane with bromine has been found to occur readily with the formation of the corresponding bromide.The reaction involves the formation of the complex RI*X2 as an intermediate and is accelerated by polar solvents.The reaction of 1-iodobicyclohexane with bromine led to rearranged products, showing that a cationic intermediate is involved.The data indicate that the IBr2- ion is one of the best of the known leaving groups for SN1 or SN2 reactions.The observation of a rapid reaction of the bridgehead bicyclooctyl iodides with bromine has led to a reexamination of the reaction of 1,4-diiodobicyclooctane with butyllithium.The previous report of the formation and trapping of the propellane in this reaction was found to be incorrect.

Temperature Effects on the Selectivity of ?-Radicals

Bent ?-radicals 3a-i, generated from alkylmercuric salts 1 and/or peresters 2, were treated with a BrCCl3/CCl4 competition system at different temperatures.Exner-analysis of these selectivity data (table 1) shows, that radicals of sp2 type 3a-d and bridgehead radicals 3e-i follow different isoselective relationships (figure 1, 2).Reversal of the selectivity row occurs at 310 and 210 K, respectively.Above of these isoselective temperatures less shielded radicals are more selective than more shielded radicals because entropy effects overcompensate enthalpy effects (table 2).Comparison with ?-radicals 6 shows, that each type of carbon radicals follows an isoselective relationship by its own.