Summary
-
1.
2-(2-Methylcyclopropyl)furan and 2-(2-cyclopropylcyclopropyl)furan add to acrolein, crotonaldehyde, and mosityl oxide in an acid medium without cleavage of the cyclopropane ring with formation of the corresponding cyclopropylfuran aldehydes and ketones.
-
2.
Aldehydes and ketones obtained in this way were subjected to Kizhner reduction with formation of 2-alkyl-5-(2-methylcyclopropyl)furans and 2-alkyl-5-(2-cyclopropylcyclopropyl)furans.
Similar content being viewed by others
Literature cited
S. M. Sherlin, A. Ya. Berlin, T. A. Serebrennikova, and F. E. Rabinovich, Zh. obshch. khimii8, 7 (1938).
K. Alder and C. H. Schmidt, Ber.76, 183 (1943).
I. N. Nazarov and T. D. Nagibina, Izv. AN SSSR. Otd. khim. n. 641 (1947).
French Pat. 972652 (1951); Chem. Abstrs.47, 1744 (1953).
Yu. K. Yur'ev, N. S. Zefirov, A. A. Shteinman, and V. M. Gurevich, Zh. obshch. khimii30, 411 (1960).
Yu. K. Yur'ev, N. S. Zefirov, A. A. Shteinman, and V. I. Ryboedov, Zh. obshch. khimii30, 3755 (1960).
N. S. Zefirov, Dissertation, Moscow (1961).
T. A. Favorskaya, N. V. Shcherbinskaya, and E. S. Golovacheva, Zh. obshch. khimii23, 1878 (1953).
B. A. Kazanskii, M. Yu. Lukina, A. I. Malyshev, V. T. Aleksanyan, and Kh. E. Sterin, Izv. AN SSSR. Otd. khim. n. 36 (1956).
K. Matsuno and K. Han, Bull. Chem. Soc. Japan, 9, 327 (1934); Chem. Abstrs.28, 7160 (1934).
A. P. Dunlop and F. N. Peters, The furans, N. Y., (1953).
N. I. Shuikin, A. D. Petrov, V. G. Glukhovtsev, and R. A. Karakhanov, Izv. AN SSSR. Otd. khim. n. 521 (1963).
Author information
Authors and Affiliations
Additional information
Raman spectra were determined by G. K. Gaivoronskaya, whom the authors thank.
Rights and permissions
About this article
Cite this article
Glukhovtsev, V.G., Zakharova, S.V. & Petrov, A.D. Preparation of aldehydes and ketones of the cyclopropylfuran series. Russ Chem Bull 12, 816–821 (1963). https://doi.org/10.1007/BF01134732
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01134732