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On the configurational stability of α-phenylseleno-alkyllithium compounds

✍ Scribed by Reinhard W. Hoffmann; Manfred Julius; Karen Oltmann

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
200 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Using a test based on kinetic resolution the aphenylseleno-alkyllithium compounds 3 have been shown to undergo enantiomer equilibration at -105 °C with a rate comparable to that of their addition to aldehydes . At -125 C in Me-THF as solvent, the a-phenylseleno-alkyllithium compounds 10 were found to be configurational stable for at least 6 hours .

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## Abstract A test based on kinetic resolution was applied to probe the configurational stability of various α‐substituted benzyllithium compounds 1. It was found that the trimethylsilyl‐ (1b), phenylsulfenyl‐ (1c), and the phenylselenyl‐substituted (1d) benzyllithium compounds enantiomerized more

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## Abstract α‐Methylbenzyllithium (6) should possess either central or planar chirality. The rate of enantiomerization of 6 at — 78^°^C was found to be faster than its addition to the amide 7, the ketone 8, or to the aldehyde 10, according to a test based on kinetic resolution. The benzyllithium co