Transformations of 2α-hydroxy-2,6,6-trimethylbicyclo[3.1.1]-heptan-3-one under conditions of acid catalysis

The transformations of 2a-hydroxy-2,6,6-trimethylbicyclo3.1.1]heptan-3-one under the conditions of acid catalysis have been studied. It has been shown that this compound can be used for the synthesis of products of various structures: a bridged bicyclic lactone (1,8,8-trimethyl-2-oxabicyclo3.2.1]octan-3-one), an aromatic compound (carvacrol), and nitrogen-containing derivatives of p-menthane such as 8-acylamino-p-menth-6-en-2-ones. The structures of the compounds synthesized were shown by the results of¹H and¹³C NMR spectroscopies.Institute of Physical Organic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 35–42, January–February, 1990.