Hp. Spielmann et al., Preparation of C70H2, C70H4, and C70H8: Three independent reduction manifolds in the Zn(Cu) reduction of C-70, J ORG CHEM, 63(26), 1998, pp. 9865-9871
This article reports the preparation of C70Hn species by Zn(Cu) reduction.
The major products were one isomer of C70H2, one major isomer of C70H4, and
one major isomer of C70H8. Several minor products were detected by UV-Vis
and/or mass spectrometry. The structures of the major products were assigne
d as 1,2-C70H2, 1,2,56,57-C70H4, and 7,19,23,27,33,37,44,53-C70H8. Interest
ingly, although the major isomer of C70H4 is generated by reduction of the
major isomer of C70H2, the major isomer of C70H8 is not generated by reduct
ion of the major isomer of C70H2 or C70H4 The evidence suggests that there
are at least three different reduction manifolds operating. One manifold in
cludes 1,2-C70H2 and 1,2,56,57-C70H4, major products in which highly pyrami
dalized bonds near the poles of C-70 are reduced. A second manifold include
s 5,6-C70H2, a minor product. The third manifold consists of a set of C70H2
, C70H4, and C70H6 species that are highly reactive and do not accumulate i
n solution. This third manifold leads to 7,19,23,27,33,37,44,53-C70H8. This
third manifold is unique in that these compounds place hydrogens on nonadj
acent carbons, a previously unobserved arrangement.