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Amidation-Sulfonation of Selected Unasaturated Monoterpenes

Wełniak M.

Polish Journal of Chemistry

2003

Vol. 77 / nr 2

203-210

Amidation-sulfonation of (+)-camphene (1), (-)-_- and (-)-_-pinene (3,4), (+)-limonene (5), (+)-2-carene (16), and (+)-carvone (21) with a mixture of 25% oleum and aceto- or propionitrile is described. Camphene (1) gave racemic exo-2-amidobornanesulfonic acids (8,9), whereas 3 and 4 produced optically active p-mentheneamidosulfonic acids (10-15). Under the same reaction conditions 1,4-addition to (+)-2-carene (16) leading to (1R,4R)-(-)-4-(1-acetylamino-1-methylethyl)-1-methyl-cyclohex-2-enesulfonic acid (17) was observed. Mixtures of diastereomeric structural terpene analogues of N-acetyltaurine were obtained from 5 and 21. Mechanisms of the investigated reactions are proposed.