H. Detert et al., WEISS-COOK CONDENSATIONS INVOLVING UNSATURATED AND TRANSANNULARLY ALKYLATED CYCLODODECANE-1,2-DIONES, Journal of organic chemistry, 60(2), 1995, pp. 353-356
(Z)-Cyclododec-7-ene-1,2-dione (4), its alkyne equivalent 7, and the s
tructurally related propellane 14 have been subjected to condensation
with dimethyl 1,3-acetonedicarboxylate. The alpha-diketones 4 and 7 un
dergo the Weiss-Cook condensation normally to deliver diquinane produc
ts in high yield. The sterically congested 14 showed no tendency to re
act. The underlying cause of the parallelism between eight- and twelve
-membered rings and the contrasting behavior of cyclodecyl analogs is
evaluated in terms of thermodynamic versus kinetic control.