STEREOCONTROLLED MULTIPLE FUNCTIONALIZATION OF CYCLOOCTENE

Gunjan Bansal

Volume 1, Issue 1 2017

Page: 45-63

Abstract

The structures of medium and large-ring molecules have been studied by dynamic NMR measurements, X-ray crystallography and semi-empirical molecular mechanics calculations.These studies indicate that although macrocyclic compounds are usually capable of existing in a large number of stable conformations, only a few of these conformations are sufficiently low in energy to be appreciably populated at normal temperatures. Cyclooctane exists largely in a boat-chair conformation (Figure 1). Cyclooctene and cyclooctanone are also conformationally biased. For cis-cyclooctene (Figure 2), the faces of the π-system are sterically very different; thus, various addition reactions occur largely from the less hindered peripheral face of the olefiniclinkage.

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