285-86-9

Usage

Uses

Bicyclo[2.1.1]hexane is used in the study of bond properties.

InChI:InChI=1/C6H10/c1-2-6-3-5(1)4-6/h5-6H,1-4H2

Upstream product

• 497-38-1 Norbornan-2-on 
• 592-42-7 1,5-Hexadien 
• 14753-34-5 2-chlorobicyclo<2.2.1>hexane 
• 38263-31-9 exo-5,syn-6-dibromobicyclo<2.1.1>hex-2-ene 
• 85407-64-3 1,4-diiodobicyclo<2.1.1>hexane 
• 73249-32-8 anti,syn-5,6-Dibromobicyclo<2.1.1>hexane 

Downstream Products

• 14548-32-4 4-methylenecyclopentene 
• 120159-43-5 2-bromobicyclo<2.1.1>hexane 
• 120159-44-6 2,2-dibromobicyclo<2.1.1>hexane 
• 120159-46-8 3-(bromo)methylenecyclopentane 
• 77379-00-1 1-bromobicyclo<2.1.1>hexane 
• 120199-36-2 trans-2,3-dibromobicyclo<2.1.1>hexane 
• 120159-45-7 2,2,3-tribromobicyclo<2.1.1>hexane 

Relevant academic research and scientific papers

Propellane. Reaction of 1,4-Diiodobicyclohexane with tert-Butyllithium and with Potassium Atoms

The synthesis of 1,4-diiodobicyclohexane (5) is described.The reaction of 5 with tert-butyllithium in hexane gave the same type of products as previously observed in the reaction of 1,4-diiodonorbornane (2) with tert-butyllithium.Evidence has been presented indicating the latter reaction to proceed via propellane as an intermediate, and it appears likely that the propellane was involved in the former reaction.The reaction of 5 with potassium atoms in the gas phase led to the formation of an unstable compound which has been isolated in a nitrogen matrix and tentatively identified as the propellane on the basis of its infrared spectrum.

Reactions and Rearrangements of 5,6-Disubstituted Bicyclohexenes

Halogenation of benzvalene (I) with either Br2 or Cl2/CCl4 gives only one adduct, anti,syn-5,6-dihalobicyclohexene, IIa or IIb.This adduct is thermally unstable and rearranges to exo,anti-4,6-dihalobicyclohexene, IIIa or IIIb (half-life at 50 deg C for IIa = 18 min; for IIb = 77 min).Treatment of IIb with 1 equiv of KCN in aqueous acetonitrile gives anti,syn-5-chloro-6-cyanobicyclohexene (IIc) and endo,endo-3,5-dicyanotricyclo2.6>hexane (IVa).IIc slowly rearranges to 6-anti-chloro-4-exo-cyanobicyclohexene (IIIc) (calculated half-l ife at 50 deg C = 1E5 min).The mechanism of the rearrangement of IIa-c to IIIa-c in light of kinetic and deuterium-labeling data as well as the mechanism of formation of IIc is discussed.When treated with KOAc in aqueous acetonitrile or AgOAc in benzene, IIb gives endo,endo-3,5-diacetoxytricyclo2.6>hexane (IVb).When IVb is treated with HCl/CCl4, it rearranges to anti,syn-5,6-diacetoxybicyclohexene (IId).When heated, both IId and IVb rearrange to exo,anti-4,6-diacetoxybicyclohexene (IIId).In contrast, IVa is thermally stable and does not rearrange in acid.