Reduction of Perfluorinated Benzocycloalkenones and Other Polyfluoroaryl Ketones to Alcohols with LiBH4

The reduction of polyfluorinated benzocycloalken-1-ones, perfluoro-2,3-dihydrobenzofuran-3-one, and perfluorinated diaryl and alkyl aryl ketones with lithium tetrahydridoborate in diethyl ether gave the corresponding alcohols. The reduction of perfluorinated 2-methyl- and 2-hydroxy-2-phenylbenzocyc...

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Veröffentlicht in:	Russian journal of organic chemistry 2022-06, Vol.58 (6), p.780-790
Hauptverfasser:	Wang, S., Golokhvastova, D. S., Zonov, Ya. V., Karpov, V. M., Mezhenkova, T. V., Gatilov, Yu. V.
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Sprache:	eng
Schlagworte:	Chemistry Chemistry and Materials Science Diethyl ether Ketones Lithium Methanol Organic Chemistry Reduction
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container_title	Russian journal of organic chemistry
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creator	Wang, S. Golokhvastova, D. S. Zonov, Ya. V. Karpov, V. M. Mezhenkova, T. V. Gatilov, Yu. V.
description	The reduction of polyfluorinated benzocycloalken-1-ones, perfluoro-2,3-dihydrobenzofuran-3-one, and perfluorinated diaryl and alkyl aryl ketones with lithium tetrahydridoborate in diethyl ether gave the corresponding alcohols. The reduction of perfluorinated 2-methyl- and 2-hydroxy-2-phenylbenzocyclobutenones was accompanied by opening of the four-membered ring with the formation of (perfluoro-2-vinylphenyl)methanol and [2-(hydroxymethyl)tetrafluorophenyl](pentafluorophenyl)methanol, respectively. Polyfluorinated benzocycloalkenediols were obtained in the reduction of dicarbonyl derivatives of perfluorinated benzocyclobutene, indan, and tetralin.
doi_str_mv	10.1134/S1070428022060045
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S. ; Zonov, Ya. V. ; Karpov, V. M. ; Mezhenkova, T. V. ; Gatilov, Yu. V.</creator><creatorcontrib>Wang, S. ; Golokhvastova, D. S. ; Zonov, Ya. V. ; Karpov, V. M. ; Mezhenkova, T. V. ; Gatilov, Yu. V.</creatorcontrib><description>The reduction of polyfluorinated benzocycloalken-1-ones, perfluoro-2,3-dihydrobenzofuran-3-one, and perfluorinated diaryl and alkyl aryl ketones with lithium tetrahydridoborate in diethyl ether gave the corresponding alcohols. The reduction of perfluorinated 2-methyl- and 2-hydroxy-2-phenylbenzocyclobutenones was accompanied by opening of the four-membered ring with the formation of (perfluoro-2-vinylphenyl)methanol and [2-(hydroxymethyl)tetrafluorophenyl](pentafluorophenyl)methanol, respectively. Polyfluorinated benzocycloalkenediols were obtained in the reduction of dicarbonyl derivatives of perfluorinated benzocyclobutene, indan, and tetralin.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428022060045</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Chemistry ; Chemistry and Materials Science ; Diethyl ether ; Ketones ; Lithium ; Methanol ; Organic Chemistry ; Reduction</subject><ispartof>Russian journal of organic chemistry, 2022-06, Vol.58 (6), p.780-790</ispartof><rights>Pleiades Publishing, Ltd. 2022</rights><rights>Pleiades Publishing, Ltd. 2022.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-8bd8503109673206bb36d84c5180a0ee63e1945c71b93ad238fa0ca7165604b43</citedby><cites>FETCH-LOGICAL-c316t-8bd8503109673206bb36d84c5180a0ee63e1945c71b93ad238fa0ca7165604b43</cites><orcidid>0000-0001-9936-0900 ; 0000-0003-0267-4976</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428022060045$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428022060045$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Wang, S.</creatorcontrib><creatorcontrib>Golokhvastova, D. 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Polyfluorinated benzocycloalkenediols were obtained in the reduction of dicarbonyl derivatives of perfluorinated benzocyclobutene, indan, and tetralin.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Diethyl ether</subject><subject>Ketones</subject><subject>Lithium</subject><subject>Methanol</subject><subject>Organic Chemistry</subject><subject>Reduction</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp1kF9LwzAUxYsoOKcfwLeAz9WbJk3Tx22oEwcb_nkuaZpunTGZSYrMT2-2CT6IT_fC_Z1zOSdJLjFcY0zozTOGAmjGIcuAAdD8KBlgBjwlpCTHcY_ndHc_Tc68X0NEMCWDZPmkml6GzhpkW7RQrtW9dZ0RQTVorMyXlVuprdBvylijPBKmQfOwUg4trN7uaSvcVqNHFfZAsGikpV1Z7dFnF1Zo1o2n9Dw5aYX26uJnDpPXu9uXyTSdze8fJqNZKglmIeV1w3MgGEpWkJikrglrOJU55iBAKUYULmkuC1yXRDQZ4a0AKQrMcga0pmSYXB18N85-9MqHam17Z-LLKmNlWfKsIDsKHyjprPdOtdXGde8xRoWh2vVZ_ekzarKDxkfWLJX7df5f9A29nXa8</recordid><startdate>20220601</startdate><enddate>20220601</enddate><creator>Wang, S.</creator><creator>Golokhvastova, D. 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V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reduction of Perfluorinated Benzocycloalkenones and Other Polyfluoroaryl Ketones to Alcohols with LiBH4</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2022-06-01</date><risdate>2022</risdate><volume>58</volume><issue>6</issue><spage>780</spage><epage>790</epage><pages>780-790</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>The reduction of polyfluorinated benzocycloalken-1-ones, perfluoro-2,3-dihydrobenzofuran-3-one, and perfluorinated diaryl and alkyl aryl ketones with lithium tetrahydridoborate in diethyl ether gave the corresponding alcohols. The reduction of perfluorinated 2-methyl- and 2-hydroxy-2-phenylbenzocyclobutenones was accompanied by opening of the four-membered ring with the formation of (perfluoro-2-vinylphenyl)methanol and [2-(hydroxymethyl)tetrafluorophenyl](pentafluorophenyl)methanol, respectively. 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subjects	Chemistry Chemistry and Materials Science Diethyl ether Ketones Lithium Methanol Organic Chemistry Reduction
title	Reduction of Perfluorinated Benzocycloalkenones and Other Polyfluoroaryl Ketones to Alcohols with LiBH4
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