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Further Investigation of the Nature of the C-Li Bond. Structures of a Phenylthiomethyllithium Complex and ofa Methylthiomethyllithium Complex

✍ Scribed by René Amsturz; Thomas Laube; W. Bernd Schweizer; Dieter Seebach; Jack D. Dunitz

Book ID
102859427
Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
754 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Phenylthiomethyllithium/N,N,N',N' -tetramethylethylenediamine (TMEDA) (1 : 1) is shown by X-ray analysis to be dimeric in the crystalline state. The structural unit contains a six-membered ring in which each Li is bonded to the terminal C atom of one thioanisole and to the S atom of the other, as well as to the two N atoms of a TMEDA. Methylthiomethyllithium/TMEDA (1 : 1) is also dimeric, but the structural unit contains a four-membered ring in which each Li is bonded to two C atoms and to the two TMEDA N atoms. An error has been detected in an earlier published electrondensity difference map for 2-lithio-2-phenyl-1, 3-dithiane/TMEDA/THF (1 : 1 : 1). The conclusion drawn then that this complex exists as a tight ion-pair in the crystal is now retracted.

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