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.
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.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
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).
Raman spectra were determined by G. K. Gaivoronskaya, whom the authors thank.
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
- Acid Medium