Conclusions
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1.
2-Acetyl-1,3-cyclopentanedione reacts with diazomethane at the carbonyl group in the ring to give the 1(3)-O-methylderivative.
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2.
2-Acetyl-1,3-cyclohexanediones react with diazomethane predominantly at the acetyl keto group.
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3.
The 1(3)-O-methyl ether of 5-phenyl-2-acetyl-1,3-cyclohexanedione reacts with diazomethane at the trigonal C(3) centers.
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Literature cited
B. Eistert, W. Reiss, and H. Wurzler, Liebigs Ann. Chem.,650, 133 (1961).
B. Eistert and H. Wurzler, Liebigs Ann. Chem.,650, 157 (1961).
B. E. Betts and W. Davey, J. Chem. Soc., 3333, 3340 (1961).
C. M. Cimarusti and J. Wolinsky, J. Org. Chem.,31, 4418 (1966).
A. A. Akhrem, A. M. Moiseenkov, F. A. Lakhvich, A. I. Poselenov, and T. M. Ivanova, Izv. Akad. Nauk SSSR, Ser. Khim., 371 (1971).
S. Forsen and M. Nilsson, Arkiv Kemi,17, 523 (1961).
E. E. Royals and J. C. Leffingwell, J. Org. Chem.,30, 1255 (1965).
A. A. Akhrem, A. M. Moiseenkov, A. I. Poselenov, V. A. Petukhov, and V. S. Bogdanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1746 (1971).
A. A. Akhrem, A. M. Moiseenkov, F. A. Lakhvich, V. I. Kadentsev, and O. S. Chizhov, Izv. Akad. Nauk SSSR, Ser. Khim., 1206 (1970).
H. Smith, J. Chem. Soc., 803 (1953).
P. M. Brown, J. S. Burton, and R. Stevens, J. Chem. Soc., 4774 (1964).
G. Nowy, W. Riedl, and H. Simon, Ber.,99, 2075 (1966).
A. A. Akhrem, A. M. Moiseenkov, and F. A. Lakhvich, Dokl. Akad. Nauk SSSR,193, 1053 (1970).
A. A. Akhrem, A. M. Moiseenkov, F. A. Lakhvich, M. B. Andaburskaya, A. V. Mkhitaryan, T. N. Sedletskaya, and V. A. Petukhov, Izv. Akad. Nauk SSSR, Ser. Khim., 594 (1971).
D. G. Farnum, J. Chickos, and P. E. Thurston, J. Amer. Chem. Soc.,88, 3075 (1966).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 143–147, January, 1972.
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Akhrem, A.A., Moiseenkov, A.M., Lakhvich, F.A. et al. Reaction of some cyclicβ-triketones with diazomethane. Russ Chem Bull 21, 128–131 (1972). https://doi.org/10.1007/BF00855670
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DOI: https://doi.org/10.1007/BF00855670