A bis(silaselenone) with two donor-stabilized Si=Se bonds from an unexpected stereoconvergent hydrolysis of a diselenadisiletane

Angewandte Chemie - International Edition

Volumn 48, Issue 22, 2009, Pages 4069-4072

  Mitra, Amitabha ^b   Wojcik, Joseph P ^b   Lecoanet, Daniel ^b   Müller, Thomas ^a   West, Robert ^b  

^a UNIVERSITY OF OLDENBURG   (Germany)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Density functional calculations; Hydrolysis; Selenium stereoconvergent reactions; Silicon

Indexed keywords

DENSITY FUNCTIONAL CALCULATIONS; DIRECT REACTIONS; ELEMENTAL SELENIUM; SILYLENES;

HYDROLYSIS; SELENIUM; SILANES;

SILICON;

EID: 70349954977     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200806389     Document Type: Article

References (13)

1. P. Arya, J. Boyer, F. Carre, R. Corriu, G. Lanneau, J. Lapasset, M. Perrot, C. Priou, Angew. Chem. 1989, 101, 1069
2. Angew. Chem. Int. Ed. Engl. 1989, 28, 1016.
3. N. Tokitoh, T. Sadahiro, K. Hatano, T. Sasaki, N. Takeda, R. Okazaki, Chem. Lett. 2002, 34.
4. T. Iwamoto, K. Sato, S. Ishida, C. Kabuto, M. Kira, J. Am. Chem. Soc. 2006, 128, 16914.
5. S. Yao, Y. Xiong, M. Brym, M. Driess, Chem. Asian J. 2008, 3, 113.
6. W. Li, N.J. Hill, A.C. Tomasik, G. Bikzhanova, R. West, Organometallics 2006, 25, 3802.
7. M. Haaf, A. Schmiedl, T. A. Schmedake, D. R. Powell, A. J. Millevolte, M. Denk, R. West, J. Am. Chem. Soc. 1998, 120, 12714.
8. For related tautomeric shifts in silanoic acid, see: Q.-G. Li, C. Deng, Y. Ren, N.-B. Wong, S.-Y. Chu, X. Wang, Int. J. Quantum Chem. 2008, 108, 142.
9. Computations were carried out using Gaussian03 (Revision D.01): M. J. Frisch et al. (see Supporting Information).
10. The addition of water across a Si-N bond is not expected to give intramolecularly stabilized silicon compounds, as calculations at the B3LYP/6-311 + G(d,p) level predict that the product of this water addition features a tetracoordinated silicon atom and that it is stabilized by a intramolecular Si-OH ⋯ NH hydrogen bridge. Details of this reaction will be published elsewhere.
11. 3.
12. see: S. Yao, M. Brym, C. van Wüllen, M. Driess, Angew. Chem. 2007, 119, 4237.
13. Angew. Chem. Int. Ed. 2007, 46, 4159.