Details
| Original language | English |
|---|---|
| Pages (from-to) | 1859-1870 |
| Number of pages | 12 |
| Journal | Chemistry - A European Journal |
| Volume | 16 |
| Issue number | 6 |
| Publication status | Published - 28 Jan 2010 |
Abstract
The reaction of some 1,1′-dialkynylferrocenes with a variety of phenols in the presence as well as in the absence of [Mo(CO)6] yields good to high yields of phenoxy[4]ferrocenophanedienes. Similar reactivity was observed with a thiophenol and with acetic acid. Reaction under basic reaction conditions led to the formation of the [4]ferrocenophanone 17. The phenoxy[4]ferrocenophanedienes obtained show dynamic behavior as a result of a torsional twist of the carbon bridge as indicated by the 1H and 13C NMR spectra. The reaction mechanism is discussed in view of recent related results of Sato et al. as well as of Pudelski et al. A vinyl cation intermediate is postulated in this context, whose relative stability is evident from the mass spectra of the compounds prepared.
Keywords
- Alkynes, Metallocenes, Phenols, Regioselectivity, Transannular addition
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - A European Journal, Vol. 16, No. 6, 28.01.2010, p. 1859-1870.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Transannular addition of phenols to 1,1′-dialkynylferrocenes
T2 - Unanticipated formation of phenoxy[4]ferrocenophanedienes
AU - Ma, Jingxiang
AU - Kühn, Björn
AU - Hackl, Thomas
AU - Butenschön, Holger
PY - 2010/1/28
Y1 - 2010/1/28
N2 - The reaction of some 1,1′-dialkynylferrocenes with a variety of phenols in the presence as well as in the absence of [Mo(CO)6] yields good to high yields of phenoxy[4]ferrocenophanedienes. Similar reactivity was observed with a thiophenol and with acetic acid. Reaction under basic reaction conditions led to the formation of the [4]ferrocenophanone 17. The phenoxy[4]ferrocenophanedienes obtained show dynamic behavior as a result of a torsional twist of the carbon bridge as indicated by the 1H and 13C NMR spectra. The reaction mechanism is discussed in view of recent related results of Sato et al. as well as of Pudelski et al. A vinyl cation intermediate is postulated in this context, whose relative stability is evident from the mass spectra of the compounds prepared.
AB - The reaction of some 1,1′-dialkynylferrocenes with a variety of phenols in the presence as well as in the absence of [Mo(CO)6] yields good to high yields of phenoxy[4]ferrocenophanedienes. Similar reactivity was observed with a thiophenol and with acetic acid. Reaction under basic reaction conditions led to the formation of the [4]ferrocenophanone 17. The phenoxy[4]ferrocenophanedienes obtained show dynamic behavior as a result of a torsional twist of the carbon bridge as indicated by the 1H and 13C NMR spectra. The reaction mechanism is discussed in view of recent related results of Sato et al. as well as of Pudelski et al. A vinyl cation intermediate is postulated in this context, whose relative stability is evident from the mass spectra of the compounds prepared.
KW - Alkynes
KW - Metallocenes
KW - Phenols
KW - Regioselectivity
KW - Transannular addition
UR - http://www.scopus.com/inward/record.url?scp=75749149282&partnerID=8YFLogxK
U2 - 10.1002/chem.200902492
DO - 10.1002/chem.200902492
M3 - Article
AN - SCOPUS:75749149282
VL - 16
SP - 1859
EP - 1870
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 6
ER -