1252669-09-2Relevant articles and documents
Efforts toward distorted spiropentanes
Su, Kuan-Jen,Mieusset, Jean-Luc,Arion, Vladimir B.,Knoll, Wolfgang,Brecker, Lothar,Brinker, Udo H.
supporting information; experimental part, p. 7494 - 7497 (2011/01/03)
Tetravinylbenzene 4 was prepared in nearly quantitative yield from commercially available tetrabromobenzene; the improved, one-step procedure now employs Suzuki-Miyaura cross-coupling conditions. Intermolecular cyclopropanation of 4 with dibromocarbene gave a series of gem-dibromide adducts. Intramolecular cyclopropanation of monoadduct 5, putatively by its methyllithium-generated cyclopropylidene(oid), produced compound 11, which features a highly distorted spiropentane having a C-C-C bond angle of 163.5°. The stability of the reported spiropentanes was investigated using DFT calculations.