Journal of Organic Chemistry p. 415 - 420 (1994)
Update date:2022-08-28
Topics:
Rico
Halvorsen
Dubrule
Lattes
Lactonization and lactamization with a novel carboxyl-activating agent, N- hexadecyl-2-chloropyridinium iodide (C16PyCl,I), were investigated. The organization of this agent in micelles in the reaction medium facilitates cyclization giving rise to a micellar effect. Under these conditions, the corresponding lactam is produced from the ω-amino acid 12-aminododecanoic acid in good yield (double that obtained with the Mukaiyama reagent, N- methyl-2-chloropyridinium iodide C1PyCl,I). On the other hand, the yield of lactone from 16-hydroxyhexadecanoic acid was the same with either carboxyl- activating agent. These results were accounted for in terms of substrate- dependent micellar effects. Because of solubility effects, the ω-amino acids and ω-hydroxy acids are not localized in comparable ways vis a vis the interface and, thus, have different reactivities. Moreover, hydrolysis of the reagents, C16PyCl,I and C1PyCl,I, was also detected. The interference of this reaction with the cyclization process was also found to depend on a micellar effect with C16PyCl,I that is not observed with C1PyCl,I.
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