IDENTIFICATION AND CHARACTERIZATION OF THE MAJOR PHOTOADDUCTS FORMED BETWEEN 1‐PHENYL‐1,3,5‐HEPTATRIYNE AND UNDECYLENIC ACID METHYL ESTER
Identifieur interne : 001329 ( Istex/Corpus ); précédent : 001328; suivant : 001330IDENTIFICATION AND CHARACTERIZATION OF THE MAJOR PHOTOADDUCTS FORMED BETWEEN 1‐PHENYL‐1,3,5‐HEPTATRIYNE AND UNDECYLENIC ACID METHYL ESTER
Auteurs : Cheon Seok Lee ; Sang Chul ShimSource :
- Photochemistry and Photobiology [ 0031-8655 ] ; 1992-03.
English descriptors
- Teeft :
- Acetylenic carbons, Adduct, Benzene, Benzene ring, Broad doublet, Chem, Chemical shift, Chemical shifts, Cheon seok, Column chromatography, Cosy, Cosy experiments, Cyclobutene, Cyclobutene ring, Cyclobutene ring protons, Cyclobutenyl, Cyclobutenyl ring, Cyclobutenyl ring protons, Double bond, Doublet, Enhancement, Ester, Geminal, Geminal proton, Hibar lichrosorb column, Hplc, Korean chem, Major photoadducts, Methyl, Methyl group, Methyl protons, Model reaction, Multiplet, Noesy, Noesy spectrum, Olefin, Overhauser, Parent uame, Particle size, Photoadduct, Photoadducts, Photocycloaddition, Photocycloaddition reaction, Photocycloaddition reactions, Photoreaction, Polyacetylenes, Proton, Regiochemical, Triple bond, Triple bonds, Uame, Vicinal, Vicinal proton.
Abstract
Abstract— The near‐UV induced photoreactions of 1‐phenyl‐1,3,5‐heptatriyne (PHT) with undecylenic(10‐undecenoic) acid methyl ester (UAME) and 1‐hexene have been investigated in n‐hexane. Four major photoadducts have been isolated in both cases and purified by normal and reverse phase liquid chromatography. The structures of these adducts were determined by mass, UV absorption, FT‐IR, 1H‐and 13C‐NMR spectral analyses, one‐and two‐dimensional nuclear Overhauser effect studies, and 1H‐1H homo‐correlation spectroscopy. All the data indicate that the adducts are cyclobutenes resulting from the [2+2] photocycloaddition of PHT to UAME and 1‐hexene.
Url:
DOI: 10.1111/j.1751-1097.1992.tb04245.x
Links to Exploration step
ISTEX:F8E2D5196EF6DC58E27E2784897CC95D6566267ALe document en format XML
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Box 150, Cheongryangni, Seoul 130–650, Korea</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence address: *To whom correspondence should be addressed.</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:F8E2D5196EF6DC58E27E2784897CC95D6566267A</idno><date when="1992" year="1992">1992</date><idno type="doi">10.1111/j.1751-1097.1992.tb04245.x</idno><idno type="url">https://api.istex.fr/ark:/67375/WNG-C2JZ9GXG-V/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">001329</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">001329</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">IDENTIFICATION AND CHARACTERIZATION OF THE MAJOR PHOTOADDUCTS FORMED BETWEEN 1‐PHENYL‐1,3,5‐HEPTATRIYNE AND UNDECYLENIC ACID METHYL ESTER</title><author><name sortKey="Lee, Cheon Seok" sort="Lee, Cheon Seok" uniqKey="Lee C" first="Cheon Seok" last="Lee">Cheon Seok Lee</name><affiliation><mods:affiliation>Department of Chemistry, Korea Advanced Institute of Science and Technology, P.O. Box 150, Cheongryangni, Seoul 130–650, Korea</mods:affiliation></affiliation></author><author><name sortKey="Shim, Sang Chul" sort="Shim, Sang Chul" uniqKey="Shim S" first="Sang Chul" last="Shim">Sang Chul Shim</name><affiliation><mods:affiliation>Department of Chemistry, Korea Advanced Institute of Science and Technology, P.O. Box 150, Cheongryangni, Seoul 130–650, Korea</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence address: *To whom correspondence should be addressed.</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Photochemistry and Photobiology</title><title level="j" type="alt">PHOTOCHEMISTRY PHOTOBIOLOGY</title><idno type="ISSN">0031-8655</idno><idno type="eISSN">1751-1097</idno><imprint><biblScope unit="vol">55</biblScope><biblScope unit="issue">3</biblScope><biblScope unit="page" from="323">323</biblScope><biblScope unit="page" to="333">333</biblScope><biblScope unit="page-count">11</biblScope><publisher>Blackwell Publishing Ltd</publisher><pubPlace>Oxford, UK</pubPlace><date type="published" when="1992-03">1992-03</date></imprint><idno type="ISSN">0031-8655</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0031-8655</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Acetylenic carbons</term><term>Adduct</term><term>Benzene</term><term>Benzene ring</term><term>Broad doublet</term><term>Chem</term><term>Chemical shift</term><term>Chemical shifts</term><term>Cheon seok</term><term>Column chromatography</term><term>Cosy</term><term>Cosy experiments</term><term>Cyclobutene</term><term>Cyclobutene ring</term><term>Cyclobutene ring protons</term><term>Cyclobutenyl</term><term>Cyclobutenyl ring</term><term>Cyclobutenyl ring protons</term><term>Double bond</term><term>Doublet</term><term>Enhancement</term><term>Ester</term><term>Geminal</term><term>Geminal proton</term><term>Hibar lichrosorb column</term><term>Hplc</term><term>Korean chem</term><term>Major photoadducts</term><term>Methyl</term><term>Methyl group</term><term>Methyl protons</term><term>Model reaction</term><term>Multiplet</term><term>Noesy</term><term>Noesy spectrum</term><term>Olefin</term><term>Overhauser</term><term>Parent uame</term><term>Particle size</term><term>Photoadduct</term><term>Photoadducts</term><term>Photocycloaddition</term><term>Photocycloaddition reaction</term><term>Photocycloaddition reactions</term><term>Photoreaction</term><term>Polyacetylenes</term><term>Proton</term><term>Regiochemical</term><term>Triple bond</term><term>Triple bonds</term><term>Uame</term><term>Vicinal</term><term>Vicinal proton</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract— The near‐UV induced photoreactions of 1‐phenyl‐1,3,5‐heptatriyne (PHT) with undecylenic(10‐undecenoic) acid methyl ester (UAME) and 1‐hexene have been investigated in n‐hexane. Four major photoadducts have been isolated in both cases and purified by normal and reverse phase liquid chromatography. The structures of these adducts were determined by mass, UV absorption, FT‐IR, 1H‐and 13C‐NMR spectral analyses, one‐and two‐dimensional nuclear Overhauser effect studies, and 1H‐1H homo‐correlation spectroscopy. 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Box 150, Cheongryangni, Seoul 130–650, Korea</json:string></affiliations></json:item><json:item><name>Sang Chul Shim</name><affiliations><json:string>Department of Chemistry, Korea Advanced Institute of Science and Technology, P.O. Box 150, Cheongryangni, Seoul 130–650, Korea</json:string><json:string>Correspondence address: *To whom correspondence should be addressed.</json:string></affiliations></json:item></author><articleId><json:string>PHP323</json:string></articleId><arkIstex>ark:/67375/WNG-C2JZ9GXG-V</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>Abstract— The near‐UV induced photoreactions of 1‐phenyl‐1,3,5‐heptatriyne (PHT) with undecylenic(10‐undecenoic) acid methyl ester (UAME) and 1‐hexene have been investigated in n‐hexane. Four major photoadducts have been isolated in both cases and purified by normal and reverse phase liquid chromatography. The structures of these adducts were determined by mass, UV absorption, FT‐IR, 1H‐and 13C‐NMR spectral analyses, one‐and two‐dimensional nuclear Overhauser effect studies, and 1H‐1H homo‐correlation spectroscopy. All the data indicate that the adducts are cyclobutenes resulting from the [2+2] photocycloaddition of PHT to UAME and 1‐hexene.</abstract><qualityIndicators><refBibsNative>true</refBibsNative><abstractWordCount>85</abstractWordCount><abstractCharCount>649</abstractCharCount><keywordCount>0</keywordCount><score>8.02</score><pdfWordCount>5503</pdfWordCount><pdfCharCount>32447</pdfCharCount><pdfVersion>1.3</pdfVersion><pdfPageCount>11</pdfPageCount><pdfPageSize>540 x 863.759 pts</pdfPageSize><pdfWordsPerPage>500</pdfWordsPerPage><pdfText>true</pdfText></qualityIndicators><title>IDENTIFICATION AND CHARACTERIZATION OF THE MAJOR PHOTOADDUCTS FORMED BETWEEN 1‐PHENYL‐1,3,5‐HEPTATRIYNE AND UNDECYLENIC ACID METHYL ESTER</title><genre><json:string>article</json:string></genre><host><title>Photochemistry and Photobiology</title><language><json:string>unknown</json:string></language><doi><json:string>10.1111/(ISSN)1751-1097</json:string></doi><issn><json:string>0031-8655</json:string></issn><eissn><json:string>1751-1097</json:string></eissn><publisherId><json:string>PHP</json:string></publisherId><volume>55</volume><issue>3</issue><pages><first>323</first><last>333</last><total>11</total></pages><genre><json:string>journal</json:string></genre></host><namedEntities><unitex><date><json:string>25/1/0.1</json:string><json:string>1992</json:string><json:string>1990</json:string></date><geogName><json:string>Ill</json:string></geogName><orgName><json:string>The Southern New England Ultraviolet Co.</json:string><json:string>Engineering Foundation</json:string><json:string>Aldrich Chemical Co.</json:string><json:string>Sigma Chemical Co.</json:string></orgName><orgName_funder></orgName_funder><orgName_provider></orgName_provider><persName><json:string>E. 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Box 150</addrLine><addrLine>Cheongryangni, Seoul 130–650, Korea</addrLine></address></affiliation></author><author xml:id="author-0001" role="corresp"><persName><forename type="first">Sang Chul</forename><surname>Shim</surname></persName><affiliation><orgName type="division">Department of Chemistry</orgName><orgName type="institution">Korea Advanced Institute of Science and Technology</orgName><address><addrLine>P.O. 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Box 150, Cheongryangni, Seoul 130–650, Korea</unparsedAffiliation></affiliation></affiliationGroup><abstractGroup><abstract type="main" xml:lang="en"><p><b>Abstract—</b> The near‐UV induced photoreactions of 1‐phenyl‐1,3,5‐heptatriyne (PHT) with undecylenic(10‐undecenoic) acid methyl ester (UAME) and 1‐hexene have been investigated in n‐hexane. Four major photoadducts have been isolated in both cases and purified by normal and reverse phase liquid chromatography. The structures of these adducts were determined by mass, UV absorption, FT‐IR, <sup>1</sup>H‐and <sup>13</sup>C‐NMR spectral analyses, one‐and two‐dimensional nuclear Overhauser effect studies, and <sup>1</sup>H‐<sup>1</sup>H homo‐correlation spectroscopy. All the data indicate that the adducts are cyclobutenes resulting from the [2+2] photocycloaddition of PHT to UAME and 1‐hexene.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>IDENTIFICATION AND CHARACTERIZATION OF THE MAJOR PHOTOADDUCTS FORMED BETWEEN 1‐PHENYL‐1,3,5‐HEPTATRIYNE AND UNDECYLENIC ACID METHYL ESTER</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>IDENTIFICATION AND CHARACTERIZATION OF THE MAJOR PHOTOADDUCTS FORMED BETWEEN 1‐PHENYL‐1,3,5‐HEPTATRIYNE AND UNDECYLENIC ACID METHYL ESTER</title></titleInfo><name type="personal"><namePart type="given">Cheon Seok</namePart><namePart type="family">Lee</namePart><affiliation>Department of Chemistry, Korea Advanced Institute of Science and Technology, P.O. Box 150, Cheongryangni, Seoul 130–650, Korea</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Sang Chul</namePart><namePart type="family">Shim</namePart><affiliation>Department of Chemistry, Korea Advanced Institute of Science and Technology, P.O. Box 150, Cheongryangni, Seoul 130–650, Korea</affiliation><affiliation>Correspondence address: *To whom correspondence should be addressed.</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>Blackwell Publishing Ltd</publisher><place><placeTerm type="text">Oxford, UK</placeTerm></place><dateIssued encoding="w3cdtf">1992-03</dateIssued><edition>Received 21 May 1991; accepted 7 August 1991</edition><copyrightDate encoding="w3cdtf">1992</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="references">27</extent><extent unit="linksCrossRef">3</extent></physicalDescription><abstract lang="en">Abstract— The near‐UV induced photoreactions of 1‐phenyl‐1,3,5‐heptatriyne (PHT) with undecylenic(10‐undecenoic) acid methyl ester (UAME) and 1‐hexene have been investigated in n‐hexane. Four major photoadducts have been isolated in both cases and purified by normal and reverse phase liquid chromatography. The structures of these adducts were determined by mass, UV absorption, FT‐IR, 1H‐and 13C‐NMR spectral analyses, one‐and two‐dimensional nuclear Overhauser effect studies, and 1H‐1H homo‐correlation spectroscopy. 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