Synthesis and structural characterization of a series of mono-O-(diphenylphosphinobenzyl)calix[6]arenes with and without tert-butyl moieties at the upper rim

Tetsuaki Fujihara, Sho Kubouchi, Yasushi Obora, Makoto Tokunaga, Kazuhiro Takenaka, Yasushi Tsuji

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

abs Synthesis and characterization of a series of mono-O- (diphenylphosphinobenzyl)calix[6]arenes are presented. The two types of calix[6]arene moieties were prepared: 1 (with tert-butyl groups at the upper rim) and 2 (without the tert-butyl groups). With regard to the position of a phosphorus atom, the diphenylphosphino group was introduced onto the ortho, meta, or para positions with the benzyl ether moiety. These phosphines as well as their oxides were fully characterized by elemental analysis, NMR measurements, and HR-ESI-MS. The NMR study indicated that 1 had a cone conformation whereas 2 was very flexible in solution. These phosphines were found to be effective ligands in Rh-catalyzed hydroformylation.

Original languageEnglish
Pages (from-to)1187-1193
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume82
Issue number9
DOIs
Publication statusPublished - Oct 5 2009
Externally publishedYes

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Phosphines
Nuclear magnetic resonance
Hydroformylation
Ether
Phosphorus
Oxides
Conformations
Cones
Ligands
Atoms
Chemical analysis
calix(6)arene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Synthesis and structural characterization of a series of mono-O-(diphenylphosphinobenzyl)calix[6]arenes with and without tert-butyl moieties at the upper rim. / Fujihara, Tetsuaki; Kubouchi, Sho; Obora, Yasushi; Tokunaga, Makoto; Takenaka, Kazuhiro; Tsuji, Yasushi.

In: Bulletin of the Chemical Society of Japan, Vol. 82, No. 9, 05.10.2009, p. 1187-1193.

Research output: Contribution to journalArticle

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AU - Kubouchi, Sho

AU - Obora, Yasushi

AU - Tokunaga, Makoto

AU - Takenaka, Kazuhiro

AU - Tsuji, Yasushi

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AB - abs Synthesis and characterization of a series of mono-O- (diphenylphosphinobenzyl)calix[6]arenes are presented. The two types of calix[6]arene moieties were prepared: 1 (with tert-butyl groups at the upper rim) and 2 (without the tert-butyl groups). With regard to the position of a phosphorus atom, the diphenylphosphino group was introduced onto the ortho, meta, or para positions with the benzyl ether moiety. These phosphines as well as their oxides were fully characterized by elemental analysis, NMR measurements, and HR-ESI-MS. The NMR study indicated that 1 had a cone conformation whereas 2 was very flexible in solution. These phosphines were found to be effective ligands in Rh-catalyzed hydroformylation.

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