Conclusions
The free-radical addition of alkanals to acrolein diacetate constitutes an efficient one-step method for the synthesis of 1,1-diacetoxyalkan-4-ones.
Similar content being viewed by others
Literature cited
General Organic Chemistry [in Russian], Vol. 2, Khimiya, Moscow (1982), pp. 637, 642, 649.
R. A. Ellison, Synthesis, 397 (1973).
O. G. Kulinkovich, I. G. Tishchenko [Tischenko], and V. L. Sorokin, Zh. Org. Khim.,20, 2548 (1984); O. G. Kulinkovich, I. G. Tishchenko, and N. V. Masalov, Synthesis, 886 (1984); O. G. Kulinkovich, I. G. Tishchenko, and V. L. Sorokin, Synthesis, 1058 (1985).
J. Stowell, J. Org. Chem.,41, 560 (1976).
M. Mikolajczyk and A. Midura, Nouv. J. Chim.,10, 567 (1986).
M. C. Mussato, D. Savoia, C. Trombini, and A. Umani-Ronchi, J. Org. Chem.,45, 4002 (1980); D. Savoia, C. Trombini, and A. Umani-Ronchi, J. Org. Chem.,47, 564 (1982); C. Boga, D. Savoia, C. Trombini, and A. Umani-Ronchi, Synthesis, 212 (1986).
K. Kondo and D. Tunemoto, Tetrahedron Lett., 1397 (1975).
T. Yoshida, T. Miyakoshi, and S. Saito, Yukagaku,33, 628 (1984).
E. Wenkert, B. L. Buckwalter, and A. A. Craveiro, J. Am. Chem. Soc.,100, 1267 (1978).
U. Valcavi, P. Farina, S. Innocenti, and V. Marotta, Synthesis, 124 (1983).
K. S. Kochhar, B. S. Bal, R. P. Deshpande, et al., J. Org. Chem.,48, 1765 (1983).
Rearrangements in Ground and Excited States, Academic Press, New York (1980), Vol. 1, p. 241.
J. K. Michie and J. A. Miller, Synthesis, 824 (1981).
L. Fieser and M. Fieser, Reagents for Organic Synthesis, 3 Vols., Wiley, New York (1967).
V. Karnozhitskii, Organic Peroxides [Russian translation], IL, Moscow (1961), p. 58.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2813–2815, December, 1988.