undergraduate thesis
Reakcija benzo (b)tiofen 1,1-dioksida i benzonitril oksida

Mario Komar (2013)
Metadata
TitleReakcija benzo (b)tiofen 1,1-dioksida i benzonitril oksida
AuthorMario Komar
Mentor(s)Nela Malatesti (thesis advisor)
Abstract
Reakcijama 1,3-dipolarne cikloadicije reagiraju dipol i dipolarofil uz nastanak peteročlanog prstena kao produkta. Oksidacijom benzo(b)tiofena, uz ledenu octenu kiselinu i vodikov peroksid, priređen je benzo(b)tiofen 1,1-dioksid, koji u 1,3-dipolarnim cikloadicijama reagira kao dipolarofil. (E)-Benzaldoksim se dobio iz benzaldehida, natrijeva hidroksida i hidroksilamin hidroklorida, a u reakcijama 1,3-dipolarne cikloadicije se koristi kao prekursor 1,3-dipola. U ovom se radu pokušala provesti 1,3-dipolarna cikloadicija korištenjem benzo(b)tiofen 1,1-dioksida kao dipolarofila te benzaldoksima iz kojeg smo očekivali stvaranje 1,3-dipola (benzonitril-oksida). Cilj je bio i usporediti odvijanje ove poznate reakcije u klasičnim uvjetima s onima u mikrovalnoj pećnici. Neočekivano, glavni produkt ovih reakcija je najvjerojatnije nastao konjugiranom adicijom umjesto 1,3-dipolarnom cikloadicijom. U radu su ponuđena objašnjenja za dobivene rezultate.
Keywordsbenzo(b)thiophene 1 1-dioxide (E)-benzaldoxime 1 3-dipolar cycloaddition dipole dipolarophile
GranterSveučilište Josipa Jurja Strossmayera u Osijeku
Odjel za kemiju
Lower level organizational unitsZavod za analitičku, organsku i primijenjenu kemiju
PlaceOsijek
StateCroatia
Scientific field, discipline, subdisciplineNATURAL SCIENCES
Chemistry
Study programme typeuniversity
Study levelundergraduate
Study programmeChemistry
Academic title abbreviationuniv. bacc. chem.
Genreundergraduate thesis
Language Croatian
Defense date2013-09-25
Parallel abstract (English)
Reactions of 1,3-dipolar cycloadditions are those where dipole and dipolarophile react together to give a 5-membered ring as a product. In this work 1,3-dipolar cycloaddition reactions between benzo(b)thiophene 1,1-dioxide and (E)-benzaldoxime have been attempted. Oxidation of benzo(b)thiophene with glacial acetic acid and hydrogen peroxide gave benzo(b)thiophene 1,1 -dioxide, which in 1,3-dipolar cycloaddition reacts as dipolarophile. (E)-Benzaldoxime was obtained from benzaldehide, sodium hydroxide and hydroxylamine hydrochloride and in reactions of 1,3-dipolar cycloaddition is used to generate 1,3-dipole. The aim of this work was also to compare known 1,3- cycloaddition reactions between these reagents by using standard conditions with those using microwave irradiation. Unexpectedly, the main product of these reactions most possibly formed by conjugated addition instead of 1,3-dipolar cycloaddition. Some explanations of the obtained results are presented in this work.
Parallel keywords (Croatian)benzo(b)tiofen 1 1-dioksid (E)-benzaldoksim 1 3-dipolarna cikloadicija dipol dipolarofil
Resource typetext
Access conditionOpen access
Terms of usehttp://creativecommons.org/licenses/by-nc-nd/3.0/hr/
URN:NBNhttps://urn.nsk.hr/urn:nbn:hr:182:755458
CommitterSanda Hasenay