99474-97-2Relevant academic research and scientific papers
Terpenes and Terpenoid Compounds, 17. - Preparation of Oxygenated Tetramethylmethenes and Tetramenthylmenthadienes
Pauluth, Detlef,Hoffmann, H. M. R.
, p. 756 - 764 (2007/10/02)
The hydroboration of rac-TM-limonene (1) (TM = tetramethyl) with 9-BBN is chemoselective and allows the functionalization of the isopropenyl side chain to give rac-TM-Δ1-p-Menthen-10-ol (4a,b), the corresponding aldehyde 5a,b, and the acid 6.Protonolysis of the product of hydroboration affords rac-TM-Δ1-p-menthene (7).Hydrochlorination of 1, epoxidation, and treatment with lithium diisopropylamide yields rac-TM-Δ1(7),8-p-menthadien-10-ol (9) which is rearranged by acid into rac-TM-Δ1,8-p-menthadien-10-ol (11).
