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Crystalline Neutral Diboron Analogues of Cyclopropanes.
- Source :
- Angewandte Chemie International Edition; 4/4/2022, Vol. 61 Issue 15, p1-6, 6p
- Publication Year :
- 2022
-
Abstract
- Although Schleyer's computations in 1979 predicted that the ground state of the parent diborirane features a planar‐tetracoordinate carbon atom (anti van't Hoff–Le Bel geometry), this work demonstrates that substitution of C coupled with N‐heterocyclic carbene (NHC) coordination provides access to isolable diborirane derivatives 3 and 4 with van't Hoff–Le Bel geometry. Species 3 and 4 are isoelectronic with cyclopropane and the highly strained B2C rings feature 2c–2e bent σ bonds. Consequently, the B−B and B−C bonds in 3 are cleaved in the presence of hydride, proton, and chalcogens. The former two reactions gave NHC‐coordinated fluorenyldihydridoborane 5 and dichlorofluorenylborane 6, respectively, whereas the latter transformations afforded novel thiaborirane 8 and selenaborirane 9. In addition, transfer hydrogenation of 3 with ammonia borane (H3N⋅BH3) led to the formation of (μ‐hydrido)diborane 7 via selective cleavage of the B−B bond. These reactivities show potential for their future application in organic synthesis. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 61
- Issue :
- 15
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 155977415
- Full Text :
- https://doi.org/10.1002/anie.202117053