Solvolytic behaviour of a primary squalene derivative

Compounds 5 (4,8,13,17,21-pentamethyl-4,8,12,16,20-docasapen- taenyl chloride and tosylate) were prepared starting from squalene and the solvolysis rates were measured in 80% (v/v) aqueous ethanol. a-Deuterium secondary kinetic isotope effects and activation parameters were calculated, and the products were determined. According to the values obtained (/CH/JCD — 0.99 ± 0.06, A H={= = 86.6 kJ mol1, A S+ = —69.3 J mol-1 K-1) and on the basis of isolated aliphatic products (11 and 14) it is concluded that the substrate follows the SN2 type displacement reaction with solvent without jt^participation of the double bond