Harder, S.; Boersma, J.; Brandsma, L.; Kanters, J.a.; Bauer, W.; Pi, R.; Schleyer, Paul v. R.; Schoellhorn, H.; Thewalt, U.:

Structure of 2-lithiobenzofuran-tmeda and 2-lithiobenzothiophene-tmeda in the solid state and in solution.

In: Organometallics, Jg. 8 (1989) ; Nr. 7, S. 1688-1696
ISSN: 0276-7333
Zeitschriftenaufsatz / Fach: Chemie
The solid-state structure of 2-lithiobenzofuran-tmeda, detd. by single-crystal x-ray diffraction, consists of dimeric species in which benzofuryl rings bridge the Li atoms and tmeda acts as chelating ligand. The O atom of one of the benzofuryl rings shows an interaction with Li. The x-ray structure of 2-lithiobenzothiophene-tmeda dimer also shows chelating tmeda ligands to be present, but no S-Li contacts. The distortion of the C(ipso)-Li-C(ipso)'-Li' ring, which also is found for dimeric phenyllithium-tmeda, is explained by steric effects. In soln. (toluene) both species are revealed by NMR to have dimeric structures with C2v symmetry. NMR shows the same to be true for 2-lithiobenzoselenophene-tmeda in toluene.

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