Synthesis of 1,3-disubstituted bicyclo[1.1.1]pentanes
β Scribed by Douglas E. Applequist; James W. Wheeler
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 123 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
For the purpose of physical studies, a variety of 1,3-disubstituted bicyclo[l.l.l]pentanes (1) were required. Although there are now numerous reports of the formation of bicyclo[l.l.l]pentanes (l), few of these provide useful yields, and there appears to be no
π SIMILAR VOLUMES
Radical chain addition of l.l.l-trichloroetha and. respectively. l,l-dichloroethane to Ll.l.llpropellans led to bicycloCl.l.llpontane derivatives 5 and 6 which could be converted by sodium amide into the acetylenes 9 and 10. Glaser type coupling afforded the diacetylenea 12 and 13.
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3-Alkylbicyclo[1.1.1]pent-1-yl Grignard reagents have been using di-or tribromoarenes, coupling products of types 10 and 11 have been obtained. The X-ray structures of four coupled with bromoarenes in the presence of catalytic amounts (0.8-2.0 mol.%) of PdCl 2 (dppf) in diethyl ether model compounds
Ab initio SCF cafwhtions have been performed on bicycle [ 1.1.1 f pentsne aird on its bridgehead anion and cation. The most striking result ties in the strong interaction between the two bridgehead sites which may be related to the properties of thi!; strained molecuie.