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Disilene Addition to C70

Published online by Cambridge University Press:  15 February 2011

S. J. Jacobs,
C. M. Rohlfing and
P. A. Cahill
S. J. Jacobs
Affiliation:
Sandia National Laboratories, Albuquerque, NM 87185–0368
C. M. Rohlfing
Affiliation:
Sandia National Laboratories, Livermore, CA, 94551–0969
P. A. Cahill
Affiliation:
Sandia National Laboratories, Albuquerque, NM 87185–0368
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Abstract

Semiempirical and ab initio Hartree Fock computational results indicate that the highly reactive dienophile tetramethyldisilene, Me2Si=SiMe2, is an excellent candidate for a novel functionalization of the equator of C70 via a [2+4] cycloaddition to the 21, 22, 23, 42 carbons. Thermal or photochemical generation of tetramethyldisilene in the presence of C70 results in similar complex mixtures in which the major product appears to be that of [2+2] cycloaddition to the 7,8 carbons of C70. A minor product clearly results from [2+2] cycloaddition to the 1,9 carbons. Both of these products are hydrolytically unstable and are converted nonspecifically to mixtures of 1,9- and 7,8-C70H2 which are also present in HPLC traces of the reaction mixtures.

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References

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