Mehta, Goverdhan and Singh, Robindro S and Priyakumar, Deva U and Sastry, Narahari G (2003) The tricyclo[18.104.22.168 2,5]pentan-3-one system: a new probe for the study of pi-facial selectivity in nucleophilic additions. In: Tetrahedron Letters, 44 (15). pp. 3101-3104.
Monosubstituted tricyclo[2.1.0.02,5]pentan-3-one derivatives have been synthesised and subjected to hydride reduction. Quite unexpectedly and in contrast to earlier observations in related systems, anti-selectivity has been encountered in these substrates. Computational studies employing various models reproduce the observed facial preference and indicate that the causative factor for the anti-preference could be the polarization of the C1---C5 strained sigma bond.
|Item Type:||Journal Article|
|Additional Information:||Copyright for this article belongs to Elsevier Science.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||26 Jul 2004|
|Last Modified:||19 Sep 2010 04:14|
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