Tetrahedron

Synthesis of Δ7-1-methylbicyclo [5, 4, 0] undecene-2, 9-dione and its condensation with acetylene

R Selvarajan, JP John, KV Narayanan, S Swaminathan

Index: Selvarajan,R. et al. Tetrahedron, 1966 , vol. 22, p. 949 - 954

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Citation Number: 11

Abstract

Michael addition of methylvinyl ketone to 2-methylcycloheptane-1, 3-dione (II) obtained by methylation of cycloheptane-1, 3-dione furnishes 2-methyl-2 (3′-oxobutyl) cycloheptane-1, 3-dione (III) which is cyclized and dehydrated in a single step to afford the title compound (Ic) in the presence of a mixture of pyrrolidine and acetic acid. A by-product isolated in this cyclization is the bridged ketol VII. Treatment of III with p-toluenesulphonic acid gives ...