Synthesis and Characterization of Some New Cycloaddition Products of Bifunctional Acetylenic Ketone

Abstract

The terephthaloylacetylene 1 yielded 2:1 addition products with hexachlorocyclopentadiene. Similar cycloaddition products with anthracene and norbornadiene were only obtained in the presence of AlCl₃ and CoBr₂/TPP/Zn respectively. In case of 1,2,3,4-tetrachloro-5,5′-dimethoxycyclopentadiene and tetraphenylcyclopentadienone the rearranged products with terephthaloylacetylene were isolated, whereas 4:1 product was obtained by the reaction of terephthaloylacetylene and cyclopentadiene.

Acknowledgment

The authors are thankful to Prof. G. N. Mathur, Director, DMSRDE, Kanpur for providing necessary facilities and encouragement to publish the work. One of the authors (R. K. Tiwari) is also thankful to Dr. P. S. Venkataramani for his guidance, help and encouragement in identifying the broader area of work. We are also thankful to CAF Division, DMSRDE and Mr Basant Lal, DRDE, Gwalior for providing the FT IR and FT NMR spectra respectively.