767357-07-3Relevant academic research and scientific papers
Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to β-pinene. Synthesis of CF3-substituted terpenoids
Dmowski, Wojciech,Ignatowska, Jolanta,Piasecka-Maciejewska, Krystyna
, p. 1147 - 1151 (2004)
Sodium dithionite effectively promotes the addition of 1-bromo-1-chloro -2,2,2-trifluoroethane to the exocyclic double bond of β-pinene. The reaction proceeded in an MeCN/H2O system to give almost quantitatively a 1:1 mixture of diastereoisomers of 4-(2-bromoisopropyl) -1-(2-chloro-3,3,3-trifluoropropyl)-cyclohexene (1). Dehydrobromination of 1 with pyridine gave a mixture of regioisomeric dienes 2 and 3, while treatment with DBU at elevated temperature resulted in total dehydrohalogenation to give trienes 4 and 5. Reduction of 1 with Bu3SnH gave 1-(2-chloro-3,3,3-trifluoropropyl)-4-(isopropyl) cyclohexene (6) which on dehydrochlorination with 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) afforded conjugated diene, 4-isopropyl-1 -(trans-3,3,3-trifluoropropenyl)-cyclohexene (7), with 50% overall yield. All the transformations proceeded with the retention of configuration at the carbon atom C-4 and the final compound 7 exhibited high optical activity.
