56170-01-5Relevant academic research and scientific papers
REACTION OF CIS-BICYCLONONADIENES WITH BROMINE AND MIXED HALOGENS
Lukovskaya, E. V.,Bobyleva, A. A.,Pekhk, T. I.,Belikova, N. A.
, p. 293 - 300 (2007/10/02)
The reaction of cis-bicyclonona-3,7-diene with bromine at -8 deg C leads to a 2:1 mixture of the isomeric tetrabromides with the trans-diaxial and trans-diequatorial arrangement of the bromine atoms in the six-membered ring and with the identical trans position for the bromine atoms in the five-membered ring.As a result of the reaction of this diene with ICl and IBr only the thermodynamically more stable trans-diequatorial isomers were isolated.In the reaction of the isomeric cis-bicyclonona-2,7-diene with bromine and with ICl only the tetrahalides with the trans-diequatorial arrangement of the bromine atoms in the six-membered ring are formed.The products from transannular cyclization were not detected at all.The mechanism and the stereochemistry of the reactions are discussed.
