Advances in bridged 1,2,4-trioxane-based chemistry. A divergent approach to oxa-heterocycles based on ambident reactivity

RIVEIRA, M. J.; LA-VENIA, A; MISCHNE, M. P.

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2010 vol. 51 p. 804 - 807

0040-4039

Heterogeneous catalytic hydrogenation of unsaturated 1,2,4-trioxanes derived from b-ionone type dienones has been investigated. Our studies revealed a versatile reactivity of trioxanic substrates that led to the development of reaction methodology for the selective manipulation of the alkene and peroxide functionalities. Depending on the catalytic system used, divergent reaction pathways can be controlled to afford either the corresponding saturated 1,2,4-trioxanes or furan structures. A mechanistic rationalisation, which accounts for the reductive behaviour of these heterocycles, is proposed.