Naslov
Intermolecular vs. intramolecular carbene reactions of a cage-functionalized cyclopentylcarbene

Autori
Marchand, Alan P. ; Kumar, Kaipenchery A. ; Mlinarić-Majerski, Kata ; Veljković, Jelena

Izvornik
Tetrahedron (0040-4020) 54 (1998), 50; 15105-15112

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Sažetak
The results of carbene reactions of pentacyclo[5.4.0.02, 6.03, 10.05, 9]undecan-8-ylidene (i.e., PCU-8-ylidene, 9) generated under different conditions by using different precursors [i.e., (i) sodium salt of PCU-8-one p-tosylhydrazone (8), (ii) PCU-8-diazirine (11), and (iii) 8, 8-dibromo-PCU (12)], are reported. PCU-8-carbene (9), generated thermally from 8, afforded homopentaprismane (17, 9.6% yield) via intramolecular C-H insertion along with other reaction products. By way of contrast, photodecomposition of 11 afforded a mixture of isomeric azines, 21a-21d, as the major reaction product. No intramolecular carbene trapping products were obtained when 9 was generated via reaction of 12 with n-BuLi.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA