Solvolytic behaviour of a primary squalene derivative

Scientific paper - Original scientific paper

• Author: Olga Kronja
• Author: Stanko Borčić
• Author: Krešimir Humski
• Author: Christopher S. Foote
• Author's institution: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of organic chemistry)
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract (english)

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.

• Language: english
• Publication type: Scientific paper - Original scientific paper
• Publication status: Published
• Peer review: Peer review - international
• Publication version: Published version
• Journal title: Croatica Chemica Acta
• Numbering: vol. 63, no. 2, pp. 193-202
• p-ISSN: 0011-1643
• e-ISSN: 1334-417X
• URN:NBN: urn:nbn:hr:163:802416
• Publication: 1990
• Document URL: https://hrcak.srce.hr/137401
• Type of resource: Text
• Access conditions: Open access
• Created on: 2020-04-30 10:37:56