Selvarajan, R. ; John, J. P. ; Narayanan, K. V. ; Swaminathan, S. (1966) Synthesis of Δ7-1-methylbicyclo[5,4,0]undecene-2,9-dione and its condensation with acetylene Tetrahedron, 22 (3). pp. 949-954. ISSN 0040-4020
Full text not available from this repository.
Official URL: http://www.sciencedirect.com/science/article/pii/0...
Related URL: http://dx.doi.org/10.1016/0040-4020(66)80069-8
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 predominantly the acid IV and only low yields of Ic. The reaction of Ic with lithium acetylide furnishes an unexpected product formulated as IX. An explanation for the differing course of ethynylation of the analogous diones Ia, Ib and Ic is given.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 70736 |
| Deposited On: | 21 Nov 2011 05:28 |
| Last Modified: | 21 Nov 2011 05:28 |
Repository Staff Only: item control page
