Organometallics p. 2424 - 2431 (1991)
Update date:2022-07-30
Topics:
Ashe III, Arthur J.
Lohr, Lawrence L.
Al-Taweel, Samir M.
The reaction of methyllithium in THF with 2,5-bis(trimethylstannyl)-1,5-hexadiene (6) affords 2,5-dilithio-1,5-hexadiene (2) via the intermediacy of lithium stannates. The similar reaction of (2Z,4Z)-2,5-bis(trimethylstannyl)-2,4-hexadiene (11) affords (2E,4E)-2,5-dilithio-2,4-hexadiene (3). The more favorable formation of 3 suggests a greater relative stability over 2. Ab initio calculations indicate that the symmetrical dilithium-bridged structure found for 3 is more favorable than the unsymmetrical dilithium-bridged structure found for 2.
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