Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1991-08-01
1993-05-18
Prescott, Arthur C.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
556110, 521 25, C07F 304
Patent
active
052118894
ABSTRACT:
A soluble highly reactive form of calcium, prepared from Ca(II) salts and a reducing agent in ethereal, polyethereal, or hydrocarbon solvents, is presented. This form of calcium can be used in the preparation of organocalcium reagents. The organocalcium reagents resulting from the reaction of the soluble highly reactive calcium with organic compounds containing either halide, cyanide, a 1,3-diene, or a polyunsaturated functionality, are stable, useful reagents for organic synthesis. The organocalcium halide reagents undergo Grignard-type reactions. They also undergo reactions with Cu(I) salts to form organocalcium cuprate reagents. The organocalcium cuprate reagents undergo a variety of cross-coupling reactions. The soluble highly reactive calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes. These bis-organocalcium reagents can undergo dialkylation reactions with .alpha.,.omega.-alkylene dihalides and dichlorosilanes to form the corresponding 3-, 5-, and 6-membered ring derivatives. The soluble highly reactive calcium also reacts with organic dihalides to form mono- or diorganocalcium compounds which can be converted into a wide variety of polymers.
REFERENCES:
patent: 4892733 (1990-01-01), Bichon et al.
patent: 4963264 (1990-10-01), Davis
patent: 4966784 (1990-10-01), Tanaka et al.
Osborn, "Synthetic Ion-Exchangers", MacMillan Co., pp. 32 & 33, (1956).
A. Alexakis et al., Tetrahedron Lett., 27, 1047 (1986).
V. Askam et al., J. Chem. Soc., 3872 (1965).
R. Baum, C&EN, 31 (Jun. 10, 1991).
S. C. Berk et al., J. Org. Chem., 53, 5789 (1988).
A. V. Bogat-skii et al., Zhurnal Obschei Khimii, 47, 2297 (1977) (English translation).
B. Bogdanovic, Acc. Chem. Res., 21, 261 (1988).
T. P. Burns et al., J. Org. Chem., 52, 3674 (1987).
J. P. Collman et al., Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA; pp. 682-738 (1987).
E. J. Corey et al., Tetrahedron Lett., 26, 6019 (1985).
G. Corfield et al., Org. Coat. Appl. Poly. Sci. Proc., 46, 445 (1981).
J. E. Dubois et al., C.R. Acad. Sci. Ser., 284, 145 (1977).
G. W. Ebert et al., J. Org. Chem., 49, 5280 (1984).
G. W. Ebert et al., J. Org. Chem., 53, 4482 (1988).
A. Ellis et al., Anal. Proc., 17, 48 (1980).
G. Erker et al., Adv. Organomet. Chem., 24, 1 (1985).
L. F. Fieser et al., J. Am. Chem. Soc., 70, 3352 (1948).
M. L. Filleux-Blanchard et al., J. Organomet. Chem., 137, 11 (1977).
P. K. Freeman et al., J. Org. Chem., 48, 879 (1983).
B. G. Gowenlock et al., J. Organomet. Chem. Library, Organomet. Chem. Rev., 3, 1 (1977).
T. P. Hanusa, Polyhedron, 9, 1345 (1990).
S. Harvey, et al., J.C.S., Chem. Commun., 652 (1988).
S. Harvey et al., J. Org. Chem., 53, 3134 (1988).
S. Itsuno, et al. J. Org. Chem., 52, 4644 (1987).
B. Jepson et al., Separation Sci. and Tech., 25, 1893 (1990).
Y. Kai et al., Chem. Lett., 1277 (1982).
N. Kawabata et al., Tetrahedron, 29, 1069 (1973).
N. Kawabata et al., J. Org. Chem., 38, 4268 (1973).
P. Knochel et al., J. Org. Chem., 53, 2390 (1988).
P. Kovacic et al., Chem. Rev., 87, 357 (1987).
H. Kroto, Pure & Appl. Chem., 62, 407 (1990).
W. E. Lindsell, Comprehensive Organometallic Chemistry, Ch. 4.1 and 4.2; Wilkinson, Stone & Abel, ed.; Pergamon Press, Oxford (1982).
B. H. Lipshutz, Tetrahedron, 40, 5005 (1984).
B. H. Lipshutz, Tetrahedron, 42, 2873 (1986).
B. H. Lipshutz, Synthesis, 325 (1987).
B. H. Lipshutz et al., Tetrahedron Lett., 28, 945 (1987).
P. Markov et al., Liebigs Ann. Chem., 704, 127 (1967).
P. Markov et al., J. Organomet. Chem., 81, 1 (1974).
P. Markov et al., Monatshefte fur Chemie, 107, 619 (1976).
M. J. McCormick et al., J.C.S. Chem. Commun., 778 (1990).
S. N. Mukherjee et al., J. Inst. Chem., 53, 300 (1981)--(Chem. Abs., 96, 689 (1982), Abstract No. 96:181042r).
S. Nishida, J. Org. Chem., 32, 2692 (1967).
J. F. Normant, Synthesis, 63 (Feb. 1972).
J. F. Normant, Pure and Appl. Chem., 50, 709 (1978).
R. A O'Brien et al., J. Org. Chem., 55, 788 (1990).
G. H. Posner, Org. Reactions (N.Y.), 19, 1 (1972).
G. H. Posner, Org. Reactions (N.Y.), 22, 253 (1975).
C. L. Raston et al., J.C.S., Chem. Commun., 1702 (1984).
R. D. Rieke et al., J. Amer. Chem. Soc., 94, 7178 (1972).
R. D. Rieke et al., J. Am. Chem. Soc., 96, 1775 (1974).
R. D. Rieke et al., ACS Symposium Series, 333, 223 (1987).
R. D. Rieke et al., Synth. Commun., 19, 1833 (1989).
R. D. Rieke, Science, 246, 1260 (1989).
R. D. Rieke et al., J. Org. Chem., 56, 3109 (1991).
F. K. Signaigo et al., J. Am. Chem. Soc., 55, 3326 (1933).
D. E. Stack et al., J. Am. Chem. Soc., 113, 4672 (1991).
J. M. Tour et al., J. Am. Chem. Soc., 113, 2309 (1991).
M. Ueda et al., Macromolecules, 24, 2694 (1991).
D. Walther et al., Naturwiss, Reihe., 34, 789 (1985)--(Chem. Abs., 105, 746 (1986), Abstract No. 105:42862z).
R. M. Wehmeyer et al., Tetrahedron Lett., 29, 4513 (1988).
T.-C. Wu et al., Tetrahedron Lett., 29, 6753 (1988).
T.-C. Wu et al., J. Org. Chem., 53, 2381 (1988).
T.--C. Wu et al., J. Org. Chem., 55, 5045 (1990).
H. Xiong et al., J. Org. Chem., 54, 3247 (1989).
T. Yamamoto et al., Bull. Chem. Soc. Japan, 51(7), 2091 (1978).
T. Yamamoto et al., Bull. Chem. Soc. Jpn., 56, 1497 (1983).
T. Yamamoto et al., Makromol. Chem., Rapid Communications, 6, 671 (1985).
Y. Yamamoto et al., J. Amer. Chem. Soc., 102, 2318 (1980).
H. Yasuda et al., Acc. Chem. Res., 18, 120 (1985).
M. C. P. Yeh et al., Tetrahedron Lett., 29, 2395 (1988).
S. H. Yu et al., J. Org. Chem., 36, 2123 (1971).
L. Zhu et al., J. Org. Chem., 56, 1445 (1991).
Board of Regents of the University of Nebraska
Prescott Arthur C.
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