Author: Alan P. Marchand

Publisher:

Published: 1988

Total Pages: 36

ISBN-13:

A significant portion of our overall research program has been concerned with the synthesis and chemistry of novel, strained polycyclic 'cage' hydrocarbon systems. The objective of our AFOSR-sponsored research program is to extend our earlier interests in the pentacyclo 5.4.0.02,6.03,10.05,9 undecane (PCUD) and pentacyclo 5.4.0.02,5,03,9.04,8 decane (1,3-bishomocubane) ring systems to include the syntheses of new polynitro derivatives of these molecules. We seek new ways to incorporate increasing numbers of NO2 groups into novel cage molecules with the ultimate goal of synthesizing a fully penitrated cage molecule, Cn(NO2)m. Our approach to these syntheses involves introducing increasing numbers of NO2 groups into a given cage system by employing a logical progression of increasingly functionalized synthetic intermediates. Thus, we are able to gauge the cumulative effects of increasing substitution (particularly NO2 substitution) upon product stability and upon the relative ease of product-forming reactions in a gradual and orderly fashion. Importantly, such approaches represent entirely new synthetic methodology for incorporating large numbers of NO2 substituents into novel, strained systems. Keywords: Cyclic compounds, Cubanes, Decanes. (MJM).