New synthesis of acylferrocene by hydroiminoacylation of the terminal olefin with ferrocenecarboxaldimine and application to polymer-supported acylferrocene

Jun Chul-Ho, Kang Jung-Bu, Kim Jin-Yong

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23 Citations (Scopus)

Abstract

Acylferrocenes were synthesized by hydroiminoacylation of the ω-olefins 1-pentene (3a), vinylferrocene (3b) and but-3-enylferrocene (3c), with the ferrocenecarboxaldimine 2, prepared from ferrocenecarboxaldehyde (1) and 2-amino-3-picoline, under the action of Wilkinson's catalyst, followed by hydrolysis of the corresponding ketimines (5a, 5b and 5c). This hydroiminoacylation was used to incorporate the ferrocenyl group into phenyl-terminated poly-butadiene (PTPB, consisting of 27% vinyl and 73% internal olefin group). 74% hydroacylation of the vinyl group in 7 was accomplished in the first catalytic reaction and in 10 the second hydroacylation completed the conversion of the vinyl group into acylferrocene.

Original languageEnglish
Pages (from-to)193-198
Number of pages6
JournalJournal of Organometallic Chemistry
Volume458
Issue number1-2
DOIs
Publication statusPublished - 1993 Oct 5

Fingerprint

Alkenes
alkenes
Olefins
Polymers
Picolines
polymers
synthesis
Butadiene
Hydrolysis
Catalysts
butadiene
hydrolysis
catalysts
ferrocenecarboxaldehyde
1,3-butadiene
vinylferrocene
ketimine
1-pentene
2-amino picoline

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

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title = "New synthesis of acylferrocene by hydroiminoacylation of the terminal olefin with ferrocenecarboxaldimine and application to polymer-supported acylferrocene",
abstract = "Acylferrocenes were synthesized by hydroiminoacylation of the ω-olefins 1-pentene (3a), vinylferrocene (3b) and but-3-enylferrocene (3c), with the ferrocenecarboxaldimine 2, prepared from ferrocenecarboxaldehyde (1) and 2-amino-3-picoline, under the action of Wilkinson's catalyst, followed by hydrolysis of the corresponding ketimines (5a, 5b and 5c). This hydroiminoacylation was used to incorporate the ferrocenyl group into phenyl-terminated poly-butadiene (PTPB, consisting of 27{\%} vinyl and 73{\%} internal olefin group). 74{\%} hydroacylation of the vinyl group in 7 was accomplished in the first catalytic reaction and in 10 the second hydroacylation completed the conversion of the vinyl group into acylferrocene.",
author = "Jun Chul-Ho and Kang Jung-Bu and Kim Jin-Yong",
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T1 - New synthesis of acylferrocene by hydroiminoacylation of the terminal olefin with ferrocenecarboxaldimine and application to polymer-supported acylferrocene

AU - Chul-Ho, Jun

AU - Jung-Bu, Kang

AU - Jin-Yong, Kim

PY - 1993/10/5

Y1 - 1993/10/5

N2 - Acylferrocenes were synthesized by hydroiminoacylation of the ω-olefins 1-pentene (3a), vinylferrocene (3b) and but-3-enylferrocene (3c), with the ferrocenecarboxaldimine 2, prepared from ferrocenecarboxaldehyde (1) and 2-amino-3-picoline, under the action of Wilkinson's catalyst, followed by hydrolysis of the corresponding ketimines (5a, 5b and 5c). This hydroiminoacylation was used to incorporate the ferrocenyl group into phenyl-terminated poly-butadiene (PTPB, consisting of 27% vinyl and 73% internal olefin group). 74% hydroacylation of the vinyl group in 7 was accomplished in the first catalytic reaction and in 10 the second hydroacylation completed the conversion of the vinyl group into acylferrocene.

AB - Acylferrocenes were synthesized by hydroiminoacylation of the ω-olefins 1-pentene (3a), vinylferrocene (3b) and but-3-enylferrocene (3c), with the ferrocenecarboxaldimine 2, prepared from ferrocenecarboxaldehyde (1) and 2-amino-3-picoline, under the action of Wilkinson's catalyst, followed by hydrolysis of the corresponding ketimines (5a, 5b and 5c). This hydroiminoacylation was used to incorporate the ferrocenyl group into phenyl-terminated poly-butadiene (PTPB, consisting of 27% vinyl and 73% internal olefin group). 74% hydroacylation of the vinyl group in 7 was accomplished in the first catalytic reaction and in 10 the second hydroacylation completed the conversion of the vinyl group into acylferrocene.

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