- Ring contraction of 1,2-dihydronaphthalenes promoted by thallium(III) in acetonitrile: A diastereoselective approach to indanes
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Trans-1,3-Disubstituted indanes are conveniently accessed by a stereoselective ring contraction of 1,2-dihydronaphthalenes upon treatment with thallium(III) nitrate (TTN) in acetonitrile. Under these conditions, the oxidative rearrangement of either di- or trisubstituted double bonds is possible. Georg Thieme Verlag Stuttgart.
- Ferraz, Helena M. C.,Carneiro, Vania M. T.,Silva Jr., Luiz F.
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experimental part
p. 385 - 388
(2009/06/18)
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- Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: A diastereoselective total synthesis of (±)-indatraline
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Equation presented A new approach for the synthesis of (±)- indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by Phl(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.
- Silva Jr., Luiz F.,Siqueira, Fernanda A.,Pedrozo, Eliane C.,Vieira, Fabiana Y. M.,Doriguetto, Antonio C.
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p. 1433 - 1436
(2008/02/02)
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- The Stereochemistry of Organometallic Compounds. XXVII. Nucleophilic and Electrophilic Substitution Reactions of Conformationally Restricted Arenechromium Compounds
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The regioselectivity of reaction of tricarbonyl(1,1-dimethylindane)chromium with selected electrophiles and nucleophiles has been shown to be influenced by the preferred conformation of the tricarbonylchromium group.Nucleophiles preferentially react at carbon atoms eclipsed by a chromium-carbonyl bond and electrophiles at carbon atoms in staggered positions.When similar reactions were attempted with some chelated arenechromium dicarbonyl phosphorus compounds only low yields of substitution products were obtained.
- Jackson, W. Roy,Rae, Ian D.,Wong, Margaret G.
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p. 303 - 315
(2007/10/02)
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