24243-17-2

Myristic acid (1a) was linked with ethylene glycol (2a), trans-1,2-cyclohexanediol (2b), and catechol (2c) to 4-benzoylbencoic acid to form the diesters 4a-c.These cyclize by photolysis to the carbinols 12, which are converted into the methyl 7- to 13-oxomyristates (5a).The ketofunctionalization of the remote CH2-groups in 1a is more selective than in the corresponding benzoylbenzoic esters 13 without the 1,2-alkanediyl or o-phenylene link.Additionally the maximum of the functionalization is shifted from the end towards the middle of the chain.The latter observation can be explained by a higher population of gauche conformations at the beginning of the chain.In CCl4 the selectivity increases slightly from 4a to 4b, c with increasing rigidity of the link.The polarity of the solvent has only a small effect on the selectivity.