Abstract
Molecular mechanics (MM2) calculations have been performed to estimate the strain energies of hydrocarbons derived from the fragments of C70 which retain C5 or C2 symmetry. There are two ways of dissecting C70 retaining C2 symmetry, C2(a) and C2(b). The key fragment along the C2(a) route is pinakene. C28H14(12). It exists in a bowl shape. Its strain energy is close to that of the corresponding C28 fragment of C70. The bowl depth was calculated to be 2.03 A at the MNDO level, and the ‘bowl-to-bowl’ inversion barrier calculated to be about 48.6 kcal mol–1, implying that this is a very rigid bowl. The strain energy build-up from the sequential placement of methylene bridges in going from dibenzo[fg,op] naphthacene (26) to pinakene was estimated. Methyl derivatives of dibenzo[fg,op]naphthacene were taken as the key precursors in this study. Strain energies of various positional isomers were also evaluated. Synthetic strategies towards pinakene are delineated.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
