T.D.J. D'silva, W. E. Walker, R. W. Manyik
1974
Citations
0
Influential Citations
3
Citations
Journal
Tetrahedron
Abstract
Abstract 2,5-Divinyltetrahydropyran ( 1 ) can be isomerized using a ruthenium trichloride- triphenylphosphine catalyst to give 3,4-dihydro-3-vinyl-6-ethyl-2H-pyran ( 2 ) and 3,4-dihydro-3- ethylidene-6-ethyl-2H-pyran ( 3 ). These products give a variety of rearranged products on treatment with acid. The course of the reactions can be controlled by reaction conditions to give 4-ethyltoluene ( 5 ) or 3-hydroxymethyl-1-octen-6-one ( 4 ) from 2 , and 3,4-dihydro-2-methyl-3-methylene-(6-ethyl-2H- pyran ( 7 ), 2,3,4-trimethyl-2-cyclohexen-1-one ( 8 ), or 3-hydroxymethyl-2-octen-6-one ( 6 ) from 3 . All of these products ( 4–8 ) can be explained as arising by the initial opening of the dihydropyran to generate an unsaturated hydroxy ketone which then cyclizes to carbocyclic products.