88829-65-6

Upstream product

• 120060-01-7 5,9-dimethyl-1-phenylundeca-5,9-dien-1-ol 
• 88829-64-5 4,8-dimethyl-4,8-decadien-1-ol 
• 100-52-7 benzaldehyde 
• 120060-00-6 10-bromo-3,7-dimethyl-2,6-decadiene 
• 57253-27-7 (E)-4-methylhex-4-en-1-ol 
• 10473-14-0 3-methyl-3-buten-2-ol 
• 58203-62-6 ethyl (E)-4-methylhex-4-enoate 
• 139448-65-0 ethyl 4,8-dimethyl-4(E),8(E)-decadienoate 
• 24268-23-3 2,6-dimethylocta-1,6-dien-3-ol 
• 27799-31-1 4-methyl-trans-4-hexenal 

Relevant academic research and scientific papers

A Case of Extended ?-Participation. Solvolysis Rate of 1-Phenyl-5,9-dimethylundeca-5,9-dienyl Chloride

The title compound (2) solvolyses nine times faster than 1-phenyl-5-methylhept-5-enyl chloride (1U) owing to participation of both aliphatic double bonds.

Hammett ρ+ Values as Kinetic Evidence for the Concerted Biomimetic Bicyclization Mechanism

Chlorides 1 (1-aryl-1-chloro-5,9-dimethyl-5,9-undecadienes) with various phenyl substituents were prepared (Y = p-OCH3, p-CH3, H, p-Br, and m-Br), and solvolysis rates were measured in 80% (v/v) aqueous ethanol and in 97% (wt/wt) aqueous 2,2,2-trifluoroethanol. The Hammett ρ+ values obtained are -1.5 and -1.8, respectively, indicating the concerted bicyclization. Comparison with ρ+ values that correspond to solvolysis of the benzylic squalene derivatives 3 (ρ+ = -1.8 and -1.6 in the same solvents) leads to the conclusion of the concerted bicyclization in 3 and may also suggest concerted bicyclization under biomimetic conditions in the natural precursor, 2,3-epoxysqualene, as well.