Conclusions
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1.
The oxidative hydroboration of 3-methylbicyclo[4.1.0]-2-heptene proceeds stereoseleetively to give cls-3-methylbicyclo[4.1.0]heptan-trans-2-ol.
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2.
The hydrogenolysis of cis-3-methylbicyclo[4.1.0]-2-heptanone gives cis-3-methylbicyclo[4.1.0]heptantrans-2-ol; the hydrogenolysis of trans-3-methylbicyclo[4.1.0]-2-heptanone leads to the formation of the alcohols trans-3-mettoylbicyclo[4.1.0]heptan-cis-2-ol and trans-3-methylbicyclo[4.1.0]heptan-trans-2-ol in a. 1.2∶1 ratio.
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Literature cited
É. Kh. Kazakova, L. N. Surkova, Z. G. Isaeva, and Sh. S. Bikeev, Dokl. Akad. Nauk SSSR,236, 363 (1977).
W. G. Dauben, G. W. Staffer, and E. J. Deviny, J. Am. Chem. Soc.,92, 6273 (1970).
D. H. Williams and N. S. Bhacca, Tetrahedron,21, 2020 (1965).
E. Toromanoff, Bull. Soc. Chim. France,1968, 2457.
K. Nakanishi, Infrared Absorption Spectroscopy, Holden-Day.
S. P. Acharya and H. C. Brown, J. Am. Chem. Soc.,89, 1925 (1967).
H. Becker, Introduction to Electronic Theory of Organic Reactions [Russian translation], Mir (1977), p. 473.
L. A. Karamysheva, E. S. Balenkova, and M. A. Gorokhova, Vest. Mosk. Univ.,4, 483 (1974).
H. C. Brown and C. P. Gard, J. Am. Chem. Soc.,83, 2951 (1961).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 875–878, April 1980.