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Lithium hexamethyldisilazide and related lithium dialkylamides are important reagents in synthetic organic chemistry. For reviews, see: d'Angelo, J. Tetrahedron 1976, 32, 2979. Heathcock, C. H. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: New York, 1980; Vol. B, Chapter 4. Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry 1991, 2, 1. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vols. 2 and 3. Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 3, Chapter 1. Snieckus, V. Chem. Rev. 1990, 90, 879.
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10544229083
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note
-
While 0.1 M pentane solutions of LiHMDS with 5.0 equiv of TMEDA and 5.0 equiv of THF contain approximately 5% TMEDA-solvated monomer (as shown in Scheme 1), the replacement of pentane with toluene affords a 60:40 dimer/monomer mixture.
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116
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0027436998
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