Conclusions
-
1.
The addition of chlorobromomalonic ester to methyl acrylate, initiated by the Fe(CO)5 + DMF system, proceeds with the cleavage of the C-Br bond in the addendum and the formation of (C2H5OOC)5CClCH2CHBr-COOCH3.
-
2.
The chlorobromo- and dichloromalonic esters when treated with Fe(CO)5 are capable of cleaving both halogen atoms and, in the absence of an unsaturated compound, form tetraethyl ethylene tetracarboxylate, while with methyl acrylate they form l, l-dicarbethoxy-2-carbomethoxycyclopropane.
Literature cited
M. Conrad and C. Brückner, Ber.,24, 2993 (1891).
T. A. Pudova, F. K. Velichko, L. I. Terekhova, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 1354.
F. K. Velichko, R. A. Amriev, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim.,1977, 1455.
C. E. Coffey, J. Am. Chem. Soc.,83, 1623 (1961).
J. Furukawa, A. Matsumura, Y. Matsuoka, and J. Kiji, Bull. Chem. Soc. Jpn.,49, 829 (1976).
E. Ciganek, J. Org. Chem.,30, 4366 (1965).
R. Pelliciari and P. Cogolli, Synthesis,1975, 269.
A. Bury and M. D. Johnson, J. Chem. Soc. Chem. Commun.,1980, 498.
T. T. Vasil'eva, F. K. Velichko, G. A. Trapeznikova, Z. A. Abdulkina, R. A. Amriev, B. V. Nelyubin, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim.,1981, 1075.
Y. Kusuyama and Y. Ikeda, Bull. Chem. Soc. Jpn.,50, 1784 (1977).
Organic Syntheses, Coll. Vol. 2 [Russian translation], IL, Moscow (1949), p. 601.
P. Krapcho and P. S. Huyffer, J. Org. Chem.,28, 2904 (1963).
S. Botros and M. Khalifa, Egypt J. Pharmac. Sci.,16, 57 (1975); Ref. Zh., Khim.,1977, 14 Zh, 44.
M. Conrad and M. Guthzeit, Ann. Chem.,214, 76 (1882).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2815–2818, December, 1981.