Synthesis and rearrangements of the pentacyclo[5.4.0.0.0.0]undecane [1,2,4-trishomocubane] ring system

Mehta, Goverdhan ; Veera Reddy, A. ; Srikrishna, A. (1986) Synthesis and rearrangements of the pentacyclo[5.4.0.0.0.0]undecane [1,2,4-trishomocubane] ring system Journal of the Chemical Society, Perkin Transactions 1 . pp. 291-297. ISSN 0300-922X

Full text not available from this repository.

Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1986...

Related URL: http://dx.doi.org/10.1039/P19860000291

Abstract

Two syntheses of the pentacyclo[5.4.0.02,6.03,10.04,8]undecane (1,2,4-trishomocubane) system are described. The first synthesis involves intramolecular photochemical [2 + 2]-cycloaddition of the triquinane bisenones (14a-d) to furnish the 1,2,4-trishomocubanediones (15a-d). The second approach is based on a boron trifluoride-diethyl ether-catalysed rearrangement of the readily available Cookson's caged diketones (16a,b) to 1,2,4-trishomocubanediones (17a,b). Thermal and acid-catalysed [2 + 2]-cycloreversions of (15a,c,d) and (17a,b) to linear fused triquinanes (14a,c,d), (20a,b) and tricyclo[5.3.1.02,6]undecane systems of current synthetic interest are also described.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:29285
Deposited On:17 Dec 2010 08:16
Last Modified:04 Jul 2012 09:39

Repository Staff Only: item control page