A comparison of the stereochemistry and kinetics of thermolysis of R-(+)-laurolenic acid, R-(+)-laurolenal, and R-(+)-laurolenol

The thermolysis of R-(+)-laurolenal (1) produces R-(+)-1,2,3-trimethylcyclopentene in high optical purity. The alcohol 3, at 297 °C, similarly produces the alkene R-(+)-4, but with mechanistic complications in that the formaldehyde produced oxidizes the alcohol 3 to the corresponding aldehyde 1. The alcohol 3-d 2 was used to show the extent of aldehyde conversion by virtue of the formation of 4-d 1 . Comparison of the decarboxylation of the acid, decarbonylation of the aldehyde, and demethanalation of the alcohol gives relative rates of 9:2:1 at 297 °C.