SYNTHESIS OF MONOFUNCTIONALIZED TETRATHIAFULVALENE (TTF) DERIVATIVES BY REACTIONS OF TETRATHIAFULVALENYLLITHIUM WITH ELECTROPHILES - X-RAY CRYSTAL-STRUCTURES OF 4 TTF DERIVATIVES BEARING AMIDE, THIOAMIDE, AND THIOESTER SUBSTITUENTS
As. Batsanov et al., SYNTHESIS OF MONOFUNCTIONALIZED TETRATHIAFULVALENE (TTF) DERIVATIVES BY REACTIONS OF TETRATHIAFULVALENYLLITHIUM WITH ELECTROPHILES - X-RAY CRYSTAL-STRUCTURES OF 4 TTF DERIVATIVES BEARING AMIDE, THIOAMIDE, AND THIOESTER SUBSTITUENTS, Chemistry of materials, 6(8), 1994, pp. 1419-1425
The synthesis is described of a series of monofunctionalized tetrathia
fulvalene (TTF) derivatives, by reactions of tetrathiafulvalenyllithiu
m with a range of electrophiles: substituents are thereby attached to
the TTF frame by carbonyl, ester, thioester, amide, and thioamide grou
ps. The X-ray crystal structures of four TTF derivatives are described
, three of them for the first time. These are 4-[O-(4-chlorobutyryl)th
iocarboxyl]-TTF(9), -[N-methylthioamido]-TTF(10),4-[N-phenylamido]-TTF
(11), and 4-[N-phenylthioamido]-TTF(12). The electron-withdrawing abi
lity of these substituents influences the geometry of the TTF ring. Wi
thin all four structures the shortest intermolecular S --- S and S ---
C contacts are coplanar with, or slightly inclined to, the TTF planes
. The structure of compound 10 provides the first example of kappa-pha
se packing in a neutral TTF donor.