Conclusions
When 1,2,8,9-diepoxy-p-menthane is reacted with HCl in ether under mild conditions, the 1,2-epoxy ring opens first in accordance with the conformational control of the reaction to form (−)-trans-2-hydroxy-1-chloro-8, 9-epoxy-trans-p-menthane from the cis dioxide or (−)-trans-1-hydroxy-2-chloro-8, 9-epoxy-trans-p-menthane from the trans dioxide. The opening of the 8,9-epoxy ring to form products of the addition of 2 moles of HCl takes place with difficulty.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 847–851, April, 1979.
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Mukhamedova, L.A., Nasybullina, F.G. & Kudryavtseva, M.I. Reaction of p-menthadiene dioxide with hydrogen chloride. Russ Chem Bull 28, 791–795 (1979). https://doi.org/10.1007/BF00923583
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DOI: https://doi.org/10.1007/BF00923583