Details
| Original language | English |
|---|---|
| Pages (from-to) | 2415-2424 |
| Number of pages | 10 |
| Journal | Journal of Organometallic Chemistry |
| Volume | 692 |
| Issue number | 12 |
| Publication status | Published - 27 Feb 2007 |
Abstract
The synthesis of tricarbonyl(N-methylisatin)chromium(0) (6) was achieved by protection of the keto functionality of the ligand as an acetal followed by complexation with tricarbonyl(naphthalene)chromium(0) and subsequent deprotection with formic acid. In order to obtain a removable substituent at nitrogen, N-methoxyethoxymethyl (N-MEM) substituted isatin 12 was prepared. Upon acetalization with trimethylformiate in methanol under acidic reaction conditions the corresponding methoxymethyl (N-MOM) derivative was unexpectedly obtained. This substitution was highly accelerated by microwave irradiation. Complexation of the N-MEM and N-MOM substituted isatin afforded only poor yields. The addition of vinylmagnesium bromide at 6 takes place not only at the keto group but also at the lactam carbonyl group. Divinylation at either one of the carbonyl functions was also achieved with the product distribution being highly dependent on the reaction time.
Keywords
- Chromium complexes, Isatin, MEM, MOM
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
- Chemistry(all)
- Inorganic Chemistry
- Materials Science(all)
- Materials Chemistry
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In: Journal of Organometallic Chemistry, Vol. 692, No. 12, 27.02.2007, p. 2415-2424.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of tricarbonyl(N-methylisatin)chromium(0) and an unanticipated transformation of a N-MEM to a N-MOM group
AU - Muschalek, Bianka
AU - Weidner, Ingo
AU - Butenschön, Holger
N1 - Funding information: This work was kindly supported by the Deutsche Forschungsgemeinschaft.
PY - 2007/2/27
Y1 - 2007/2/27
N2 - The synthesis of tricarbonyl(N-methylisatin)chromium(0) (6) was achieved by protection of the keto functionality of the ligand as an acetal followed by complexation with tricarbonyl(naphthalene)chromium(0) and subsequent deprotection with formic acid. In order to obtain a removable substituent at nitrogen, N-methoxyethoxymethyl (N-MEM) substituted isatin 12 was prepared. Upon acetalization with trimethylformiate in methanol under acidic reaction conditions the corresponding methoxymethyl (N-MOM) derivative was unexpectedly obtained. This substitution was highly accelerated by microwave irradiation. Complexation of the N-MEM and N-MOM substituted isatin afforded only poor yields. The addition of vinylmagnesium bromide at 6 takes place not only at the keto group but also at the lactam carbonyl group. Divinylation at either one of the carbonyl functions was also achieved with the product distribution being highly dependent on the reaction time.
AB - The synthesis of tricarbonyl(N-methylisatin)chromium(0) (6) was achieved by protection of the keto functionality of the ligand as an acetal followed by complexation with tricarbonyl(naphthalene)chromium(0) and subsequent deprotection with formic acid. In order to obtain a removable substituent at nitrogen, N-methoxyethoxymethyl (N-MEM) substituted isatin 12 was prepared. Upon acetalization with trimethylformiate in methanol under acidic reaction conditions the corresponding methoxymethyl (N-MOM) derivative was unexpectedly obtained. This substitution was highly accelerated by microwave irradiation. Complexation of the N-MEM and N-MOM substituted isatin afforded only poor yields. The addition of vinylmagnesium bromide at 6 takes place not only at the keto group but also at the lactam carbonyl group. Divinylation at either one of the carbonyl functions was also achieved with the product distribution being highly dependent on the reaction time.
KW - Chromium complexes
KW - Isatin
KW - MEM
KW - MOM
UR - http://www.scopus.com/inward/record.url?scp=34247341704&partnerID=8YFLogxK
U2 - 10.1016/j.jorganchem.2007.02.034
DO - 10.1016/j.jorganchem.2007.02.034
M3 - Article
AN - SCOPUS:34247341704
VL - 692
SP - 2415
EP - 2424
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 12
ER -