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- Title
1,3-Diazasilabicyclo[1.1.0]butane with a Long Bridging N−N Bond.
- Authors
Xiao, Xu‐Qiong; Dong, Zhaowen; Li, Zhifang; Yan, Chenting; Lai, Guoqiao; Kira, Mitsuo
- Abstract
A 1,3-diazasilabicyclo[1.1.0]butane ( 1) is synthesized as thermally stable crystals by using the cycloaddition reaction of an isolable dialkylsilylene with aziadamantane. The bridge N−N bond length of 1 (1.70 Å) is the longest among those of known N−N singly-bonded compounds, including side-on bridged transition-metal dinitrogen complexes. The compound 1 is intact in air but moisture sensitive. No reaction occurs with hydrogen, even under pressure at 0.5 MPa. Irradiation of 1 with light gives an isomer quantitatively by N−N and adamantyl C−C bond cleavage. The origin of the remarkable N−N bond elongation is ascribed to significant interaction between a Si−C σ* and Ν−Ν π and σ orbitals as determined by DFT calculations of model compounds.
- Subjects
SILYLENES; RING formation (Chemistry); BRIDGING ligands; COVALENT bonds; X-ray diffraction; AMINES; CHEMICAL bond lengths; REACTIVITY (Chemistry)
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 11, p3822
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201511493