From: Carl Feynman (carlf@atg.com)
Date: Mon Jul 21 1997 - 10:44:44 MDT
At 08:00 PM 7/20/97 +0200, Eugene Leitl wrote:
>
>>Carbon-carbon bond formation via Wurtz-class metalloorganyles
>(Grignard, lithium, copper, or whatever) reactions is a
>time-honoured technique of organic synthesis.
>...
>A possible scenario would involve cooking a wild mixture of
>different polycyclic alkanes ... Once in place, they
>crosslink by multiple C-C instantly, irreversibly. (Using
>phlegmatized surface groups, this should be worthwhile to try
>even in solvated phase, xref autoassembly via complementary
>surfaces).
I don't know what Wurtz-class metalloorganyles are, but I assume that you
mean C-C bond formation by activated carbon nucleophiles (Grignard etc).
This proceeds by back side attack with consequent steric inversion. This
is of course impossible with a polycyclic diamondoid target.
What other reactions might work for subunit linkage? Diels-alder won't work
because it requires highly unsaturated reactants, which are not permitted by
the harsh conditions for rearrangement into diamondoid building-blocks.
Radicals might work, though any easily removed radical group would probably
also be destroyed in the building-block phase.
--CarlF
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