Oxymercuration-demercuration of limonene

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作者：

M Bambagiotti，A Franco，F Vincieri，SA Coran

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摘要：

The oxymercuration-demercuration procedure, in aqueous THF, was applied to limonene (1) to investigate the behavior of its two double bonds. It was shown that cis-1,8-terpin (cis-7) and 1,8-cineole (9) were produced when a 1:2 limonene-Hg(OAc)2 mole ratio was used. Production of α-terpineol (5) together with cis-7 and 9 was observed when the limonene-Hg(OAc)2 mole ratio was reduced (1:1 and 1:0.5). The reactions were very fast and no oxidative side process was evident. Further information on the reactivity of the endocyclic limonene double bond was given by comparison of the behavior of 5 and 1-p-menthene under the same reaction conditions. The results indicate that the first hydroxyl group that adds onto the external limonene double bond enhances the reactivity of the internal double bond, promoting a high overall reaction rate. Moreover, the unexpected production of both cis-7 and 9 indicates that, although the first hydroxyl group is in an ideal position to react, via a six-membered ring, to give the corresponding cyclic ether 9, the latter only partially forms, the major product being the corresponding diol cis-7.

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DOI：

10.1021/jo00919a021

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年份：

2002