18993-10-7Relevant academic research and scientific papers
Regioselective Functionalization of Non-Activated CH-bonds, 2. Photochemical Functionalization of the Myristoyl Group in 1,2-Alkanediyl and o-Phenylene 1-(4-Benzoylbenzoate) 2-Myristates
Dors, Bernhard,Luftmann, Heinrich,Schaefer, Hans J.
, p. 761 - 776 (2007/10/02)
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.
