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Directing effects in nitration of 1-adamantyl bearing aromatic ketones

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dc.title Directing effects in nitration of 1-adamantyl bearing aromatic ketones en
dc.contributor.author Vícha, Robert
dc.contributor.author Kuřitka, Ivo
dc.contributor.author Rouchal, Michal
dc.contributor.author Ježková, Veronika
dc.contributor.author Zierhut, A.
dc.relation.ispartof Arkivoc
dc.identifier.issn 1424-6376 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2009
utb.relation.volume 2009
utb.relation.issue 12
dc.citation.spage 60
dc.citation.epage 80
dc.type article
dc.language.iso en
dc.publisher ARKAT USA, Inc. en
dc.relation.uri http://www.arkat-usa.org/get-file/30256/
dc.subject Aromatic ketones en
dc.subject 1-adamantyl en
dc.subject electrophylic substitution en
dc.subject nitration en
dc.subject regioselectivityes en
dc.description.abstract Byla studována nitrace čtyř různých 1-adamantyl(alkylaryl)ketonů za různých podmínek. Ve všech případech bylo nalezeno neobvyklé množství ortho regioisomerů. Na základě experimentálních výsledků a semi-empirických výpočtů byl navržen mechanismus nitrací studovaných ketonů, zahrnující předrovnováhu protonované a nitroniované formy výchozího ketonu. cs
dc.description.abstract Nitration of four 1-adamantyl bearing aromatic ketones with mixed acid, acetyl nitrate, silver nitrate and guanidine nitrate was studied under various conditions. The ketones with conjugated carbonyl group or with a benzyl group were examined and a considerably high amount of ortho isomer was observed in all cases. The proportion of ortho nitration showed the same trends for both examined groups of ketones. Unprecedently, the ortho isomer was formed quantitatively upon the reaction of 1-(1-adamantyl)-3-phenylpropan-2-one with acetyl nitrate in acetic anhydride. Influence of electronic, steric and complexation effect of carbonyl group on regioselectivity is discussed. An alternative reaction pathway including complexation of nitrating agent and a pre-equilibrium of protonated and nitronium coordinated carbonyl in particular is suggested to play crucial and general role in nitrations of aromatic carbonyl compounds. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1001016
utb.identifier.rivid RIV/70883521:28110/09:63508148!RIV10-MSM-28110___
utb.identifier.obdid 43861005
utb.identifier.scopus 2-s2.0-77953190762
utb.identifier.wok 000273295600006
utb.source j-riv
utb.contributor.internalauthor Vícha, Robert
utb.contributor.internalauthor Kuřitka, Ivo
utb.contributor.internalauthor Rouchal, Michal
utb.contributor.internalauthor Ježková, Veronika
utb.contributor.internalauthor Zierhut, A.
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