Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes
1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were...
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| Autor*in: |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1973 |
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| Reproduktion: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
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| Übergeordnetes Werk: |
in: Tetrahedron - Amsterdam : Elsevier, 29(1973), 21, Seite 3341-3346 |
| Übergeordnetes Werk: |
volume:29 ; year:1973 ; number:21 ; pages:3341-3346 |
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NLEJ175832730 |
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| 245 | 1 | 0 | |a Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes |
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| 520 | |a 1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. | ||
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(DE-627)NLEJ175832730 (DE-599)GBVNLZ175832730 DE-627 ger DE-627 rakwb eng Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes 1973 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Mitsui, S. oth Senda, Y. oth Suzuki, H. oth Sekiguchi, S. oth Kumagai, Y. oth in Tetrahedron Amsterdam : Elsevier 29(1973), 21, Seite 3341-3346 (DE-627)NLEJ175783357 (DE-600)2007072-X 0040-4020 nnns volume:29 year:1973 number:21 pages:3341-3346 http://linkinghub.elsevier.com/retrieve/pii/S0040-4020(01)93486-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 29 1973 21 3341-3346 |
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(DE-627)NLEJ175832730 (DE-599)GBVNLZ175832730 DE-627 ger DE-627 rakwb eng Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes 1973 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Mitsui, S. oth Senda, Y. oth Suzuki, H. oth Sekiguchi, S. oth Kumagai, Y. oth in Tetrahedron Amsterdam : Elsevier 29(1973), 21, Seite 3341-3346 (DE-627)NLEJ175783357 (DE-600)2007072-X 0040-4020 nnns volume:29 year:1973 number:21 pages:3341-3346 http://linkinghub.elsevier.com/retrieve/pii/S0040-4020(01)93486-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 29 1973 21 3341-3346 |
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(DE-627)NLEJ175832730 (DE-599)GBVNLZ175832730 DE-627 ger DE-627 rakwb eng Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes 1973 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Mitsui, S. oth Senda, Y. oth Suzuki, H. oth Sekiguchi, S. oth Kumagai, Y. oth in Tetrahedron Amsterdam : Elsevier 29(1973), 21, Seite 3341-3346 (DE-627)NLEJ175783357 (DE-600)2007072-X 0040-4020 nnns volume:29 year:1973 number:21 pages:3341-3346 http://linkinghub.elsevier.com/retrieve/pii/S0040-4020(01)93486-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 29 1973 21 3341-3346 |
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(DE-627)NLEJ175832730 (DE-599)GBVNLZ175832730 DE-627 ger DE-627 rakwb eng Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes 1973 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Mitsui, S. oth Senda, Y. oth Suzuki, H. oth Sekiguchi, S. oth Kumagai, Y. oth in Tetrahedron Amsterdam : Elsevier 29(1973), 21, Seite 3341-3346 (DE-627)NLEJ175783357 (DE-600)2007072-X 0040-4020 nnns volume:29 year:1973 number:21 pages:3341-3346 http://linkinghub.elsevier.com/retrieve/pii/S0040-4020(01)93486-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 29 1973 21 3341-3346 |
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(DE-627)NLEJ175832730 (DE-599)GBVNLZ175832730 DE-627 ger DE-627 rakwb eng Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes 1973 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Mitsui, S. oth Senda, Y. oth Suzuki, H. oth Sekiguchi, S. oth Kumagai, Y. oth in Tetrahedron Amsterdam : Elsevier 29(1973), 21, Seite 3341-3346 (DE-627)NLEJ175783357 (DE-600)2007072-X 0040-4020 nnns volume:29 year:1973 number:21 pages:3341-3346 http://linkinghub.elsevier.com/retrieve/pii/S0040-4020(01)93486-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 29 1973 21 3341-3346 |
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Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes |
| abstract |
1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. |
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1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. |
| abstract_unstemmed |
1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism. |
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<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">NLEJ175832730</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20210706010305.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">070505s1973 xx |||||o 00| ||eng c</controlfield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)NLEJ175832730</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)GBVNLZ175832730</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Stereochemistry and mechanism of the hydrogenation of substituted cyclopentenes</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">1973</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">z</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zu</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">1,2- and 2,3-disubstituted cyclopentenes were hydrogenated with several transition metal catalysts. The hydrogenation of 1,2-disubstituted cyclopentenes gave preferably the cis products with Raney Ni, whereas 2,3-disubstituted cyclopentenes gave preferably the trans isomers. The trans products were favoured in the hydrogenation of 1,2- and 2,3-dialkylcyclopentenes with Pt or Pd catalysts. A detailed product analysis of the hydrogenation of 1,2-dialkylcyclopentenes indicates that the double bond migration occurred to form 2,3-dialkylcyclopentenes in advance of the hydrogenation. In contrast, 1-methyl-2-phenylcyclopentene gave predominantly the cis product irrespective of the kind of catalyst. These results suggest the formation of a π-benzylic species during the course of the reaction. The mechanism is discussed in terms of the modified Horiuti-Polanyi mechanism.</subfield></datafield><datafield tag="533" ind1=" " ind2=" "><subfield code="f">Elsevier Journal Backfiles on ScienceDirect 1907 - 2002</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Mitsui, S.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Senda, Y.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Suzuki, H.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Sekiguchi, S.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Kumagai, Y.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">in</subfield><subfield code="t">Tetrahedron</subfield><subfield code="d">Amsterdam : Elsevier</subfield><subfield code="g">29(1973), 21, Seite 3341-3346</subfield><subfield code="w">(DE-627)NLEJ175783357</subfield><subfield code="w">(DE-600)2007072-X</subfield><subfield code="x">0040-4020</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:29</subfield><subfield code="g">year:1973</subfield><subfield code="g">number:21</subfield><subfield code="g">pages:3341-3346</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">http://linkinghub.elsevier.com/retrieve/pii/S0040-4020(01)93486-6</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_H</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">ZDB-1-SDJ</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_NL_ARTICLE</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">29</subfield><subfield code="j">1973</subfield><subfield code="e">21</subfield><subfield code="h">3341-3346</subfield></datafield></record></collection>
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