Abstract
A procedure was developed for the synthesis of 1,1′-bishydroperoxydi(C11-C15-cycloalkyl) peroxides based on homocoupling of geminal 11–15-membered bis(hydroperoxy)cycloalkanes in the presence of BF3⋅OEt2.
Similar content being viewed by others
References
P. Busch and P. R. Story, Synthesis, 1970, 181.
M. J. C. Harding and D. M. Whalen, Ind. Ing. Chem., Prod. Res. Dev., 1975, 14, 232.
R. Story and P. Busch, in Advances in Organic Chemistry, Ed. E. C. Taylor, Wiley, New York, 1972, Vol. 8, 67.
G. A. Razuvaev, V. S. Etlis, N. I. Kirillov, and E. M. Samarina, Vysokomol. Soedin., 1961, 3, 1176 [Polym. Sci. USSR, 1961, 3 (Engl. Transl.)].
V. L. Antonovskii, A. F. Nesterov, and O. K. Lyashenko, Zh. Prikl. Khim., 1967, 40, 2555 [J. Appl. Chem. USSR, 1967, 40 (Engl. Transl.)].
V. L. Antonovskii, A. F. Nesterov, Kh. B. Tsubina, and I. M. Al'shits, Uspekhi khimii perekisnykh soedinenii i autookisleniya [Advances in Chemistry of Peroxide Compounds and Autooxidation], Khimiya, Moscow, 1969, 100 pp. (in Russian).
T. Ledaal and T. Solbjor, Acta Chem. Scand., 1967, 21, 1658.
T. Dashes and T. Ledaal, Acta Chem. Scand., 1971, 25, 1906.
K. Paul, P. R. Story, P. Busch, and J. R. Sanderson, J. Org. Chem., 1976, 41, 1283.
A. O. Terent'ev, A. V. Kutkin, M. M. Platonov, Yu. N. Ogibin, and G. I. Nikishin, Tetrahedron Lett., 2003, 44, 7359.W
A. O. Terent'ev, A. V. Kutkin, M. M. Platonov, I. I. Vorontsov, M. Yu. Antipin, Yu. N. Ogibin, and G. I. Nikishin, Izv. Akad. Nauk., Ser. Khim., 2004, 650 [Russ. Chem. Bull., Int. Ed., 2004, 53, 681].
Structure Correlation, Eds H.-B. Burgi and J. D. Dunitz, VCH, Weinheim, Vol. 2, 783.
P. Groth, Acta Chem. Scand., 1975, 29, 783.
C. W. Jefford, Synth. Commun., 1990, 20, 2589.
G. M. Sheldrick, SHELXTL-97, Program for Solution and Refinement of Crystal Structure, Bruker AXS Inc., Madison, WI-53719, USA, 1997.
Author information
Authors and Affiliations
Additional information
Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1182–1185, May, 2005.
Rights and permissions
About this article
Cite this article
Terent'ev, A.O., Kutkin, A.V., Platonov, M.M. et al. Synthesis of 1,1′-bishydroperoxydi(cycloalkyl) peroxides by homocoupling of 11–15-membered gem-bis(hydroperoxy)cycloalkanes in the presence of boron trifluoride. Russ Chem Bull 54, 1214–1218 (2005). https://doi.org/10.1007/s11172-005-0383-4
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-005-0383-4