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Structure and Reactivity of Benzyl Compounds - Stephan Koller

In modern organometallic chemistry the deprotonation of benzyl compounds is still a worthwhile goal, as the benzylic anion is very variable showing different structure patterns and reactivity.

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Structure of Benzyllithium Compounds[1,3]  Reactivity of Benzyl Substituted Coumpounds[2,3]
- mode of aggregation - stereoselective deprotonation
- hybridisation of the carbanion: sp2 vs sp3 - exchange of R2
- charge distribution and coordination pattern of the benzyl anion

 

 

[1] a) C. Strohmann, K. Lehmen, A. Ludwig, D. Schildbach, Organometallics 2001, 20, 4138-4140; b) H. Ott, C. Däschlein, D. Leusser, D. Schildbach, T. Seibel, D. Stalke, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 11901-11911; c) C. Strohmann, T. Seibel, D. Schildbach, J. Am. Chem. Soc. 2004, 126, 9876-9877; d) S.G. Koller, U. Kroesen, C. Strohmann, Chem. Eur. J. 2015, 21, 641-647.

[2] C. Strohmann, D.H.M. Buchold, T. Seibel, K. Wild, D. Schildbach, Eur. J. Inorg. Chem. 2003, 3453-3463.

[3] S.G. Koller, Dissertation, TU Dortmund, 2015.