Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1995-10-20
1998-04-14
Barts, Samuel
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 54, 560 39, 560127, 562509, 562459, 549274, 549454, 568329, 540467, 564 47, C07C 6976
Patent
active
057393761
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of application PCT/EP/01079 filed Apr. 7, 1994.
Fullerenes are cage-like carbon allotropes of the formula (C.sub.20+2m) (where m=a natural number). They contain twelve five-membered rings and also any number, but at least two, six-membered rings of carbon atoms. Although this class of compound was discovered only in 1985 by Kroto and Smalley (Nature, 1985, 318, 162) and Kratschmer and Huffman only reported the preparation of macroscopic amounts of C.sub.60 in 1990 (Nature 1990, 347, 354), such compounds have very quickly attracted wide interest and within a very short time have become the subject of numerous research studies (see, for example, G. S. Hammond, V. J. Kuck (Editors), Fullerenes, American Chemical Society, Washington D.C. 1992 and Accounts of Chemical Research, March edition 1992).
Since a high potential is expected of this class of substances, for example in the fields of optoelectronics and research on active compounds, efforts have already been made to form derivatives, in particular of C.sub.60 (see, for example, H. Schwarz, Angew, Chem. 1992, 104, 301 and F. Wudl et al. in G. S. Hammond, V. J. Kuck (Editors), Fullerenes, American Chemical Society, Washington D.C. 1992 and Accounts of Chemical Research, March edition 1992).
Some experiments on forming derivatives succeeded in isolating defined products. Examples are the reactions of fullerenes in 1.3 dipolar cycloadditions with diazo compounds (e.g. F. Wudl et al., Acc. Chem. Res. glycosylidenecarbenes (e.g. A. Vasella et al., Angew. Chem. 1992, 104, 1383).
Further examples are the addition of nucleophiles such as organolithium and organomagnesium compounds (e.g. A. Hirsch et al., Angew. Chem. 1992, 104, 808).
It was desirable to synthesize fullerene derivatives containing structural units having those functional groups which are known to have applications in the field of research on active compounds, which can also be utilized for the construction of new polymer materials and which improve the physical properties, such as solubility or polarity, of the fullerene derivatives.
It has long been known that 1,3-dicarbonyl compounds such as malonic esters and .beta.-ketoesters have proven useful in the synthesis of active compounds (e.g. Organikum 16, intended edition 1986, pages 393, 413, 414).
The linking of acid C-H compounds, such as malonic esters or .beta.-ketoesters, with activated olefins is known as the Michael edition (e.g. Organikum 16, intended edition 1986, page 507). It has now been found that well-defined fullerene derivatives can be obtained by reacting fullerenes, for example, with the anions of 2-halocarbonyl compounds.
The invention provides a fullerene derivative of the formula I ##STR2## in which the symbols and indices have the following meanings: F: is a fullerene radical of the formula C.sub.(20+2m) where m=20, 25, 28, 29; CONRR.sup.1, CHO, COR, CN, P(O)(OR).sub.2 and SO.sub.2 R, where R, R.sup.1 are each a straight-chain or branched, aliphatic radical (C.sub.1 to C.sub.20) which may be unsubstituted or monosubstituted or polysubstituted by identical or different substituents, in which radical up to every third CH.sub.2 unit can be replaced by O or NR.sup.4, where R.sup.4 is (C.sub.1 -C.sub.20)-alkyl or benzyl, or a benzyl radical or phenyl radical which can be unsubstituted or substituted by from 1 to 5 substituents R, OH, OR, COOR, OCOR, SO.sub.3 H, SO.sub.2 Cl, F, Cl, Br, NO.sub.2 and CN or together are ##STR3## or are different from one another and are each COR, R or H, or are different from one another and are each COR/R or F/Cl/Br, where R is as defined above, or are different from one another and are each NO.sub.2, R.sup.3 or H, where R.sup.3 is an unsubstituted, monosubstituted or polysubstituted aliphatic radical (C.sub.1 to C.sub.20);
Preference is given to compounds of the formula I in which the symbols and indices have the following meanings: 29, P(O)(OR).sub.2, COOH, CN, where R is a straight-chain or branched, aliphatic radical (C.sub.1 to C.sub.20) which may be unsubstituted or mon
REFERENCES:
Bingel, Carsten, "Cyclopropanierung von Fullerenen", Chem. Ber. 1993, 126:1957-1959.
Barts Samuel
Hoechst Aktiengesellschaft
LandOfFree
Fullerene derivatives, methods of preparing them and their use does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fullerene derivatives, methods of preparing them and their use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fullerene derivatives, methods of preparing them and their use will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-636479