- New Syntheses of Cyclopentapyrene 3,4-Oxide and 4-Pyrenylacetic Acid
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New syntheses of cyclopentapyrene 3,4-oxide (CPPE) and 4-pyrenylacetic acid, a key intermediate in the synthesis of cyclopentapyrene and CPPE, are described starting from 1,2,3,6,7,8-hexahydropyrene. 4-Pyrenylacetic acid is prepared from the corresponding alcohol, 2-(4-pyrenyl)ethanol, by applying two mild oxidation reactions. 4-Pyrenylacetaldehyde was obtained by N-chlorosuccinimide dimethyl sulfide oxidation, and this was converted smoothly to the desired 4-pyrenylacetic acid by silver oxide oxidation, an approach that has potential for a new route to arylacetic acids from arylethanols.The epoxide CPPE is prepared by cyclization of the 3,4-trans-dihydroxycyclopentapyrene via its monotosylate, prepared in situ, with powdered sodium hydroxide.
- Sahali, Y.,Skipper, P. L.,Tannenbaum, S. R.
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- Syntheses of unsymmetrically N,N′-bis (substituted)-4,13-diaza-18-crown-6-ether derivatives as a new electron donor-spacer-acceptor triad
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A simple and general synthetic strategy potentially applicable for the preparation of a wide variety of unsymmetrically N,N′-bis(substituted)-4, 13-diaza-18-crown-6-ether derivatives was reported.
- Morimoto, Minoru,Fukui, Keijiro,Kawasaki, Norioki,Iyoda, Tomokazu,Shimidzu, Takeo
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- Convenient synthesis of cyclopentapyrene and 3,4-dihydrocyclopentapyrene. The reactivity of the pyrene dianion
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The reactivity of the pyrene dianion has been investigated.Initial attack by electrophiles on the pyrene dianion has been shown to take place exclusively at the 4(9)-position, leading to monoanions (11,15) which can be converted into 9-substituted 1,9-dihydropyrene derivatives (12,16).The latter can be rearranged to give the novel 4-substituted 4,5-dihydropyrene derivatives (13,17), which provide access to 4-substituted pyrene derivatives (14,5).Cyclopentapyrene (1) and 3,4-dihydrocyclopentapyrene (2), two widespread environmental contaminants, have been synthesizedfrom pyrene in four (64percent) and in five (62percent), respectiveliy, utilizing the chemical properties of the pyrene dianion.In these easy and straightforward syntheses the thus far unknown 4,5-dihydro-4-pyreneacetic acid (17) plays a major role.
- Tintel, C.,Cornelisse, J.,Lugtenburg, J.
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- Synthesis of Cyclopentapyrene via a High Yield One-step Preparation of Pyren-4-ylacetic Acid from Pyrene
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In a single step and in 95percent yield pyrene can be converted into pyren-4-ylacetic acid from which subsequently cyclopentapyrene (CPP) can be obtained in an overall yield of 60percent.
- Tintel, Kees,Lugtenburg, Johan,Cornelisse, Jan
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p. 185 - 186
(2007/10/02)
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