A. Dastan et al., BROMINATION OF DECALIN AND ITS DERIVATIVES .9. HIGH-TEMPERATURE BROMINATION, Journal of organic chemistry, 62(12), 1997, pp. 4018-4022
Thermal and photobromination of decalin, 1, was studied, trans,cis,tra
ns-2,5,7,9-tetrabromooctalin 2, was obtained as the major product alon
g with smaller amounts of bromonaphthalene derivatives. The structures
of the products were determined by H-1- and C-13-NMR data and single
X-ray structural analysis. Bromination of the two decalin derivatives
9 and 10 results in the formation of single isomers 11 and 12, respect
ively. The three tetrabromides 2, 11, and 12 were shown by molecular m
echanics calculations to be the most stable stereoisomer in each case.
The formation of these tetrabromides under thermodynamic control is p
ostulated.