Insertion Reaction of a Silylene into a N-H Bond of Hydrazine and a [1+4] Cycloaddition with Diphenyl Hydrazone
2009 | journal article. A publication with affiliation to the University of Göttingen.
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Insertion Reaction of a Silylene into a N-H Bond of Hydrazine and a [1+4] Cycloaddition with Diphenyl Hydrazone
Jana, A.; Roesky, H. W.; Schulzke, C. & Samuel, P. P. (2009)
Organometallics, 28(22) pp. 6574-6577. DOI: https://doi.org/10.1021/om9007086
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- Authors
- Jana, Anukul; Roesky, Herbert W.; Schulzke, Carola; Samuel, Prinson P.
- Abstract
- The reaction of a stable six-membered N-heterocyclic silylene, LSi (1) [L = CH{(C=CH(2))(CMe)(2,6-iPr(2)C(6)H(3)N)(2)}], with hydrazine and its derivatives is described. 1 reacts with hydrazine to form LSi(H)NHNH(2) (2) under N-H bond insertion of the silylene. The reaction of 1 and N-methyl hydrazine results exclusively in the formation of LSi(H)NHNHMe (3). Treatment of 1 with an equimolar amount of diphenyl hydrazone in toluene yields the dearomatized siloxy-indolin-1-amine 4 in almost quantitative yield rather than the insertion product at the N-H bond of the NH(2) group. Compounds 2-4 were characterized by microanalysis, multinuclear NMR, and IR spectroscopy. Compounds 2 and 4 are confirmed by X-ray structural analysis with the result that 2 and 4 are both monomeric and the silicon center of each resides in a distorted tetrahedral environment.
- Issue Date
- 2009
- Status
- published
- Publisher
- Amer Chemical Soc
- Journal
- Organometallics
- ISSN
- 0276-7333
- Sponsor
- Deutsche Forschungsgemeinschaft