Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems

Azhakar R, Ghadwal R, Roesky HW, Mata RA, Wolf H, Herbst-Irmer R, Stalke D (2013)
Chemistry - A European Journal 19(11): 3715-3720.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Azhakar, Ramachandran; Ghadwal, RajendraUniBi ; Roesky, Herbert W.; Mata, Ricardo A.; Wolf, Hilke; Herbst-Irmer, Regine; Stalke, Dietmar
Abstract / Bemerkung
Three‐ and five‐membered rings that bear the (Si‐C‐S) and (Si‐C‐C‐C‐S) unit have been synthesized by the reactions of LSiCl (1; L=PhC(NtBu)2) and L′Si (2; L′=CH{(CCH2)(CMe)(2,6‐iPr2C6H3N)2}) with the thioketone 4,4′‐bis(dimethylamino)thiobenzophenone. Treatment of 4,4′‐bis(dimethylamino)thiobenzophenone with LSiCl at room temperature furnished the [1+2]‐cycloaddition product silathiacyclopropane 3. However, reaction of 4,4′‐bis(dimethylamino)thiobenzophenone with L′Si at low temperature afforded a [1+4]‐cycloaddition to yield the five‐membered ring product 4. Compounds 3 and 4 were characterized by NMR spectroscopy, EIMS, and elemental analysis. The molecular structures of 3 and 4 were unambiguously established by single‐crystal X‐ray structural analysis. The room‐temperature reaction of 4,4′‐bis(dimethylamino)thiobenzophenone with L′Si resulted in products 4 and 5, in which 4 is the dearomatized product and 5 is formed under the 1,3‐migration of a hydrogen atom from the aromatic phenyl ring to the carbon atom of the CS unit. Furthermore, the optimized structures of probable products were investigated by using DFT calculations.
Erscheinungsjahr
2013
Zeitschriftentitel
Chemistry - A European Journal
Band
19
Ausgabe
11
Seite(n)
3715-3720
ISSN
09476539
Page URI
https://pub.uni-bielefeld.de/record/2951037

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Azhakar R, Ghadwal R, Roesky HW, et al. Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems. Chemistry - A European Journal. 2013;19(11):3715-3720.
Azhakar, R., Ghadwal, R., Roesky, H. W., Mata, R. A., Wolf, H., Herbst-Irmer, R., & Stalke, D. (2013). Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems. Chemistry - A European Journal, 19(11), 3715-3720. https://doi.org/10.1002/chem.201203242
Azhakar, Ramachandran, Ghadwal, Rajendra, Roesky, Herbert W., Mata, Ricardo A., Wolf, Hilke, Herbst-Irmer, Regine, and Stalke, Dietmar. 2013. “Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems”. Chemistry - A European Journal 19 (11): 3715-3720.
Azhakar, R., Ghadwal, R., Roesky, H. W., Mata, R. A., Wolf, H., Herbst-Irmer, R., and Stalke, D. (2013). Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems. Chemistry - A European Journal 19, 3715-3720.
Azhakar, R., et al., 2013. Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems. Chemistry - A European Journal, 19(11), p 3715-3720.
R. Azhakar, et al., “Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems”, Chemistry - A European Journal, vol. 19, 2013, pp. 3715-3720.
Azhakar, R., Ghadwal, R., Roesky, H.W., Mata, R.A., Wolf, H., Herbst-Irmer, R., Stalke, D.: Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems. Chemistry - A European Journal. 19, 3715-3720 (2013).
Azhakar, Ramachandran, Ghadwal, Rajendra, Roesky, Herbert W., Mata, Ricardo A., Wolf, Hilke, Herbst-Irmer, Regine, and Stalke, Dietmar. “Reaction of N-Heterocyclic Silylenes with Thioketone: Formation of Silicon-Sulfur Three (Si-C-S)- and Five (Si-C-C-C-S)-Membered Ring Systems”. Chemistry - A European Journal 19.11 (2013): 3715-3720.

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