C-C Bond Cleavage of 8-Quinolinyl Alkyl Ketone by σ,η3-Allyl Rhodium(III) Complex

Dae Yon Lee, Yeong Gweon Lim, Chul-Ho Jun

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Bis(ethylene)rhodium(I) chloride dimer reacted with vinylcyclopropane to give σ,η3-allylrhodium(III) complex 3. Complex 3 underwent C-C bond cleavage of 8-quinolinyl ethyl ketone 11, to form η3-1,3-dimethylallylrhodium(III) complex 8, which was reductively eliminated by trimethyl phosphite to give 8-quinolinyl-1-methylbut-2-enyl ketone (10). More sterically hindered 8-quinolinyl alkyl ketones were allowed to react with complex 3 to afford corresponding alkenes as well as a mixture of complex 8 and η3-1-ethylallyl rhodium(III) complex 19, identified as 10 and 8-quinolinyl-pent-2-enyl ketone (20) after reductive elimination. 8-Quinolinyl alkyl ketone bearing a sterically hindered alkyl group showed less reactivity for C-C bond cleavage and higher 20/10 ratio compared with those having a less sterically hindered alkyl group, such as 8-quinolinyl ethyl ketone (11).

Original languageEnglish
Pages (from-to)824-827
Number of pages4
JournalBulletin of the Korean Chemical Society
Volume18
Issue number8
Publication statusPublished - 1997 Dec 1

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Rhodium
Ketones
trimethyl phosphite
Bearings (structural)
Alkenes
Complex Mixtures
Dimers
Chlorides

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "C-C Bond Cleavage of 8-Quinolinyl Alkyl Ketone by σ,η3-Allyl Rhodium(III) Complex",
abstract = "Bis(ethylene)rhodium(I) chloride dimer reacted with vinylcyclopropane to give σ,η3-allylrhodium(III) complex 3. Complex 3 underwent C-C bond cleavage of 8-quinolinyl ethyl ketone 11, to form η3-1,3-dimethylallylrhodium(III) complex 8, which was reductively eliminated by trimethyl phosphite to give 8-quinolinyl-1-methylbut-2-enyl ketone (10). More sterically hindered 8-quinolinyl alkyl ketones were allowed to react with complex 3 to afford corresponding alkenes as well as a mixture of complex 8 and η3-1-ethylallyl rhodium(III) complex 19, identified as 10 and 8-quinolinyl-pent-2-enyl ketone (20) after reductive elimination. 8-Quinolinyl alkyl ketone bearing a sterically hindered alkyl group showed less reactivity for C-C bond cleavage and higher 20/10 ratio compared with those having a less sterically hindered alkyl group, such as 8-quinolinyl ethyl ketone (11).",
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C-C Bond Cleavage of 8-Quinolinyl Alkyl Ketone by σ,η3-Allyl Rhodium(III) Complex. / Lee, Dae Yon; Lim, Yeong Gweon; Jun, Chul-Ho.

In: Bulletin of the Korean Chemical Society, Vol. 18, No. 8, 01.12.1997, p. 824-827.

Research output: Contribution to journalArticle

TY - JOUR

T1 - C-C Bond Cleavage of 8-Quinolinyl Alkyl Ketone by σ,η3-Allyl Rhodium(III) Complex

AU - Lee, Dae Yon

AU - Lim, Yeong Gweon

AU - Jun, Chul-Ho

PY - 1997/12/1

Y1 - 1997/12/1

N2 - Bis(ethylene)rhodium(I) chloride dimer reacted with vinylcyclopropane to give σ,η3-allylrhodium(III) complex 3. Complex 3 underwent C-C bond cleavage of 8-quinolinyl ethyl ketone 11, to form η3-1,3-dimethylallylrhodium(III) complex 8, which was reductively eliminated by trimethyl phosphite to give 8-quinolinyl-1-methylbut-2-enyl ketone (10). More sterically hindered 8-quinolinyl alkyl ketones were allowed to react with complex 3 to afford corresponding alkenes as well as a mixture of complex 8 and η3-1-ethylallyl rhodium(III) complex 19, identified as 10 and 8-quinolinyl-pent-2-enyl ketone (20) after reductive elimination. 8-Quinolinyl alkyl ketone bearing a sterically hindered alkyl group showed less reactivity for C-C bond cleavage and higher 20/10 ratio compared with those having a less sterically hindered alkyl group, such as 8-quinolinyl ethyl ketone (11).

AB - Bis(ethylene)rhodium(I) chloride dimer reacted with vinylcyclopropane to give σ,η3-allylrhodium(III) complex 3. Complex 3 underwent C-C bond cleavage of 8-quinolinyl ethyl ketone 11, to form η3-1,3-dimethylallylrhodium(III) complex 8, which was reductively eliminated by trimethyl phosphite to give 8-quinolinyl-1-methylbut-2-enyl ketone (10). More sterically hindered 8-quinolinyl alkyl ketones were allowed to react with complex 3 to afford corresponding alkenes as well as a mixture of complex 8 and η3-1-ethylallyl rhodium(III) complex 19, identified as 10 and 8-quinolinyl-pent-2-enyl ketone (20) after reductive elimination. 8-Quinolinyl alkyl ketone bearing a sterically hindered alkyl group showed less reactivity for C-C bond cleavage and higher 20/10 ratio compared with those having a less sterically hindered alkyl group, such as 8-quinolinyl ethyl ketone (11).

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