NEW ROUTE TO 4,4,6,7-TETRASUBSTITUTED PENTACYCLO[6.3.0.0(2,6).0(3,10).0(5,9)]UNDECANES

Authors
ALEKSANDROV AM BOURNE SA KRAWIEC M PEHK TJ PETRENKO AE WATSON WH
Citation
Am. Aleksandrov et al., NEW ROUTE TO 4,4,6,7-TETRASUBSTITUTED PENTACYCLO[6.3.0.0(2,6).0(3,10).0(5,9)]UNDECANES, Tetrahedron, 50(29), 1994, pp. 8597-8602
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
29
Year of publication
1994
Pages
8597 - 8602
Database
ISI
SICI code
0040-4020(1994)50:29<8597:NRT4P>2.0.ZU;2-0
Abstract
The reactions of -2,7-dioxotetraeyclo[6.3.0.0(4,11).0(5,9)]undecane wi th organomagnesium halides are investigated as a method of preparing u nusual tetrasubstituted pentacycloundecanes (D-3-trishomocubanes). The tetrasubstituted pentacycloundecanes have been characterized and prod uct geometries confirmed by NMR and X-ray crystal structure analysis. oxy-4-phenyl-6-methyl-7-bromo-(D-3)-trishomocubane (11) exhibits a ste rically locked phenyl group with a rotation barrier > 17 kcal/mol whic h should make possible the preparation of stable rotational isomers wi th o- or m-substituted phenyl groups.