A Germylene/Borane Lewis Pair and the Remarkable C=O Bond Cleavage Reaction toward Isocyanate and Ketone Molecules
2016 | journal article. A publication with affiliation to the University of Göttingen.
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A Germylene/Borane Lewis Pair and the Remarkable C=O Bond Cleavage Reaction toward Isocyanate and Ketone Molecules
Li, J.; Li, B.; Liu, R.; Jiang, L.; Zhu, H.; Roesky, H. W. & Dutta, S. et al. (2016)
Chemistry - A European Journal, 22(41) pp. 14499-14503. DOI: https://doi.org/10.1002/chem.201603544
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Details
- Authors
- Li, Jiancheng; Li, Bin; Liu, Rui; Jiang, Liuyin; Zhu, Hongping; Roesky, Herbert W.; Dutta, Sayan; Koley, Debasis; Liu, Weiping; Ye, Qingsong
- Abstract
- A germylene/borane Lewis pair (2) was prepared from a 1,1-carboboration of amidinato phenylethynylgermylene (1) by B(C6F5)(3). Compound 2 reacted with iPrNCO and (4-MeOC6H4)C(O)Me, respectively, with cleavage of the C=O double bond. In the first instance, O and iPrNC insert separately into the Ge-B bond to yield a GeBC2O-heterocycle (3) and a GeBC3-heterocycle (4). In the second case (4-MeOC6H4)(Me)C inserts into the Ge-N bond of 2 while O is incorporated in the Ge-B bond to form a Ge-centered spiroheterocycle (5). The reaction of 2 with tBuNC to give 6, which has almost the same structure as 4, proved the formation of the isonitrile during transformation from 2 and iPrNCO to 3 and 4. The kinetic study of the reaction of 2 and iPrNCO gave evidence of proceeding through a GeBC3O-heterocycle intermediate. In addition, a DFT study was performed to elucidate the reaction mechanism.
- Issue Date
- 2016
- Status
- published
- Publisher
- Wiley-v C H Verlag Gmbh
- Journal
- Chemistry - A European Journal
- ISSN
- 1521-3765; 0947-6539