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α-Olefins (1-octadecene (1 ) and 1-hexadecene ( 2 )), when reacted with N -bromosuccinimide (NBS ( 3 )) and long-chain fatty acids (such as lauric acid ( 4 ), myristic acid ( 5 ), or palmitic acid ( 6 )) in dichloromethane at room temperature, resulted in ca. 50% conversion of the α-olefin, yielding the wax esters: dodecanoic acid 1-bromomethyl heptadecyl ester ( 7a )/dodecanoic acid 2-bromomethyl octadecyl ester ( 7b ); tetradecanoic acid 1-bromomethyl heptadecyl ester ( 8a )/tetradecanoic acid 2-bromomethyl octadecyl ester ( 8b ); hexadecanoic acid 1-bromomethyl heptadecyl ester ( 9a )/hexadecanoic acid 2-bromomethyl octadecyl ester ( 9b ); dodecanoic acid 1-bromomethyl pentadecyl ester ( 10a )/dodecanoic acid 2-bromomethyl hexadecyl ester ( 10b ); tetradecanoic acid 1-bromomethyl pentadecyl ester ( 11a )/tetradecanoic acid 2-bromomethyl hexadecyl ester ( 11b ); and hexadecanoic acid 1-bromomethyl pentadecyl ester ( 12a )/hexadecanoic acid 2-bromomethyl hexadecyl ester ( 12b ).
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Singh et al. (2007) studied this question.
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