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
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<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. All the data indicate that the adducts are cyclobutenes resulting from the [2+2] photocycloaddition of PHT to UAME and 1‐hexene.</div>
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<profileDesc><abstract xml:lang="en" style="main"><p><hi rend="bold">Abstract—</hi>
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, <hi rend="superscript">1</hi>
H‐and <hi rend="superscript">13</hi>
C‐NMR spectral analyses, one‐and two‐dimensional nuclear Overhauser effect studies, and <hi rend="superscript">1</hi>
H‐<hi rend="superscript">1</hi>
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>
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<titleGroup><title type="tocHeading1">Original Article</title>
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<correspondenceTo>*To whom correspondence should be addressed.</correspondenceTo>
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<contentMeta><unparsedEditorialHistory><i>Received</i>
21 <i>May</i>
1991; <i>accepted</i>
7 <i>August</i>
1991</unparsedEditorialHistory>
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<titleGroup><title type="main">IDENTIFICATION AND CHARACTERIZATION OF THE MAJOR PHOTOADDUCTS FORMED BETWEEN 1‐PHENYL‐1,3,5‐HEPTATRIYNE AND UNDECYLENIC ACID METHYL ESTER</title>
</titleGroup>
<creators><creator creatorRole="author" xml:id="cr1" affiliationRef="#a1"><personName><givenNames>Cheon Seok</givenNames>
<familyName>Lee</familyName>
</personName>
</creator>
<creator creatorRole="author" xml:id="cr2" affiliationRef="#a1" corresponding="yes"><personName><givenNames>Sang Chul</givenNames>
<familyName>Shim</familyName>
</personName>
</creator>
</creators>
<affiliationGroup><affiliation xml:id="a1"><unparsedAffiliation>Department of Chemistry, Korea Advanced Institute of Science and Technology, P.O. Box 150, Cheongryangni, Seoul 130–650, Korea</unparsedAffiliation>
</affiliation>
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<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>
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<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>
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<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>
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<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>
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<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. All the data indicate that the adducts are cyclobutenes resulting from the [2+2] photocycloaddition of PHT to UAME and 1‐hexene.</abstract>
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