Summary
-
1.
An investigation was made of the stereochemistry of the addition of hydrogen cyanide, acetylene, and ethylmagnesium bromide to 3-t-butylcyclohexanone and of the reduction of 3-t-butylcyclohexanone with sodium borohydride. The configurations were proved to the then formed 3-t-butyl-1-hydroxycyclohexanecarbonitriles, 3-t-butyl-1-ethynylcyclohexanols, 3-t-butyl-1-ethylcyclohexanols, and their derivatives (hydroxy acids, acetic esters).
-
2.
The reactions investigated go more selectively in the case of 3-t-butylcyclohexanone than in the case of 3-methylcyclohexanone.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
I. N. Nazarov, A. V. Kamernitskii, and A. A. Akhrem, Zh. obshch. khimii28, 1458 (1958).
A. A. Akhrem and A. V. Kamernitskii, Izv. AN SSSR. Otd. khim. n.1959, 748.
A. V. Kamernitskii and A. A. Akhrem, Zh. obshch. khimii28, 754 (1959).
M. I. Batuev, A. A. Akhrem, A. D. Matveeva, and I. N. Nazarov, Dokl. AN SSSR,117, 423 (1957).
M. I. Batuev, A. A. Akhrem, A. D. Matveeva, A. V. Kamernitskii, and I. N. Nazarov, ibid.,120, 779 (1958).
M. I. Batuev, A. A. Akhrem, A. V. Kamernitskii, and A. D. Matveeva, Izv. AN SSSR. Otd. khim. n.1959, 1695.
M. I. Batuev, A. A. Akhrem, and A. D. Matveeva, ibid.,1960, 538.
M. I. Batuev, A. A. Akhrem, A. V. Kamernitskii, and A. D. Matveeva, Izv. AN SSSR. Otd. khim. n. ibid.,1961, 1813.
A. Skita and W. Faust, Ber.64,1931, 2878.
P. Anziani and R. Cornubert, Bull. Soc. chim. France (5),12, 359 (1945).
R. Cornubert, Compt. Rend. Akad. sci.,237, 469 (1953).
W. Hückel and A. Hubbele, Ann.,613, 27 (1958).
K. D. Hardy and R. I. Wicker, J. Amer. Chem. Soc.,80, 640 (1958).
W. G. Dauben, G. I. Fonken, and D. S. Noyce, ibid.,78, 2579 (1956).
W. G. Dauben and R. E. Bozak, J. Organ. Chem.24, 1596 (1959).
W. Hückel, M. Maier, E. Jordan, and W. Seeger, Ann.616, 46 (1958).
D. S. Noyce and D. B. Denney, J. Amer. Chem. Soc.72, 5743 (1950).
L. Eliel and S. Ro, J. Amer. Chem. Soc.79, 5992 (1957).
S. Winstein and N. I. Holness, ibid.,77, 5562 (1955).
A. V. Kamernitskii and A. A. Akhrem, Uspekhi khimii.30, 145 (1961).
G. F. Hennion and F. X. O'Shea, J. Amer. Chem. Soc.80, 614 (1958).
I. Houlihan, J. Organ. Chem.27, 3860 (1962).
G. Stork and W. N. White, J. Amer. Chem. Soc.78, 4699 (1956).
A. Pasqual, J. Sistare, and A. Reags, J. Chem. Soc.1949 (1943).
I. N. Nazarov and A. A. Akhrem, Zh. obshch. khimii28, 1791 (1958).
D. H. Barton and R. Cookson, Quart. Rev.10, 44 (1956); H. Orloff, Chem. Revs.54, 347 (1954).
A. A. Akhrem, A. I Kuznetsova, Yu. A. Titov, and I. S. Levina, I zv. AN SSSR, Otd. khim. n.,1962, 657
E. A. Mistryukov, J. Chromatogr.9, 311 (1962).
K. Dimroth and K. Resin, Ber.75, 322 (1942).
Bartlett and G. F. Woods, J. Amer. Chem. Soc.,62, 2933 (1940).
F. Whitmore and G. W. Pedlow, J. Amer. Chem. Soc.,63, 758 (1941).
Author information
Authors and Affiliations
Additional information
This article is published in accordance with a resolution of the Conference of Chief Editors of Journals of the Academy of Sciences of the USSR, July 12, 1962, as a dissertation paper by A. M. Prokhoda.
The authors thank V. A. Vaver for the analysis of samples on the Pye Chromatograph.
Translated from Izvestiya Akademii Nauk SSSR, Setiya Khimicheskaya, No. 6, pp. 1060–1068, June, 1964
Rights and permissions
About this article
Cite this article
Prokhoda, A.M., Kamernitskii, A.V. & Akhrem, A.A. Stereochemistry of nucleophilic additions to the carbonyl group Communication 6. Reactions of 3-t-butylcyclohexanone. Russ Chem Bull 13, 984–990 (1964). https://doi.org/10.1007/BF01141652
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01141652