7-Cis isomers of retinal via 7-cis- and 7,9-dicis-β-C18-tetraene ketones: new geometric isomers of vitamin A and carotenoids - I

Ramamurthy, V. ; Liu, R. S. H. (1975) 7-Cis isomers of retinal via 7-cis- and 7,9-dicis-β-C18-tetraene ketones: new geometric isomers of vitamin A and carotenoids - I Tetrahedron, 31 (3). pp. 201-206. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/0...

Related URL: http://dx.doi.org/10.1016/0040-4020(75)85066-6

Abstract

Based catalyzed condensation of 7-cis- or 7,9-dicis-β-ionylideneacetaldehyde with acetone gave either 7-cis or 7,9-dicis-β-C18-tetraene ketone. Reaction of the tetraene ketone mixture with diethyl cyanomethylphosphonate gave a mixture of 4 isomers of retinonitrile, all believed to have the 7-cis geometry. Partial redution of the retinonitrile mixture with di-isobutylaluminum hydride gave a mixture of retinal isomers. Repeated column chromatography resulted in partial separation of the retinal isomers. Based on NMR data the geometry of the isomers prepared are believed to be 7-cis, 7,13-dicis, and 7,9,13-tricis.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:91467
Deposited On:21 May 2012 12:03
Last Modified:21 May 2012 12:03

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