1.
J Org Chem
; 77(7): 3468-74, 2012 Apr 06.
Artigo
em Inglês
| MEDLINE
| ID: mdl-22420624
RESUMO
cis,anti,cis-Tricyclo[7.4.0.0(2,8)]tridec-10-ene (13TCT) undergoes [1,3] sigmatropic rearrangements at 315 °C in the gas phase to the si product 1 and to the sr product 2 with si/sr = 2.1. The dominant thermal isomerization process, however, is epimerization at C8 to afford product 3. That stereomutation at C8 occurs 50% faster than the si and sr shifts combined.