Mehta, Goverdhan ; Padma, S. (1991) Synthetic studies towards prismanes: Seco-[6]-prismane Tetrahedron, 47 (37). pp. 7783-7806. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)81936-0
Abstract
The first synthesis of seco-[6]-prismane 5, the closest, one-bond-away secologue of [6]-prismane 4, from the readily available Diels-Alder adduct of 1,5-cyclooctadiene and dimethoxytetrachlorocyclopentadiene is described. The key chemical operations in the 17 step sequence are (i) 4+2-cycloaddition of singlet oxygen 20 → 22, (ii) boron mediated fragmentation 47 → 14 and (iii) intramolecular 2+2-photocycloaddition 14 → 49. The methodology outlined here offers opportunities for further elaboration to [6]-prismane as well as several of its homo- and secologues.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Seco-[6]-prismane; Pentacyclic Dimer of Benzene; Photooxygenation; Intramolecular 2+2-photocycloaddition; Boronate Fragmentation |
| ID Code: | 29181 |
| Deposited On: | 17 Dec 2010 08:27 |
| Last Modified: | 17 Dec 2010 08:27 |
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