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Literature cited
H. J. Günther and V. Jäger, “Reaction of iodine with non-conjugated dienes: iodocyclization promoted by a remarkable gem-dialkyl effect,” Tetrahedron Lett., No. 29, 2359–2542 (1977).
I. G. Traynham and H. H. Hsieh, “Addition reactions of cis, trans-1,5-cyclooctadiene,” J. Org. Chem.,38, No. 5, 868–872 (1973).
J. N. Labows and D. Swern, “Addition of pseudohalogens to 1,5-cyclooctadiene,” J. Org. Chem.,37, No. 19, 3004–3006 (1972).
H. J. Franz, W. Hobold, R. Höhn, et al., “Electrophilic addition to cis,cis-1,5-cyclooctadiene,” J. Prakt. Chem.,312, No. 4, 622–634 (1970).
A. S. Koz'min, V. N. Kirin, V. V. Zhdankin, and N. S. Sefirov, “Doping-addition of arylsulfenyl chlorides to derivates of tricyclo-[4.2.2.02,5]deca-3,7-diene,” in: IX-th International Symposium on Chemistry of Organic Compounds. Summaries of Lectures [in Russian], Riga (1980), p. 41.
J. H. Liu, G. A. Ganger, and P. Kovacic, “Synthesis and reactions of 3- and 3,7-substituted bicyclo[3.3.1]nonanes,” J. Org. Chem.,38, No. 3, 543–546 (1973).
T. Mari, K. Kimoto, M. Kawanisi, and H. Nozaki, “Preparation and reactions of 1,5-polymethylene-bridged 3,7-dimethylenebicyclo[3.3.1]-nonan-9-ones,” Tetrahedron Lett, No. 41, 3653–3656 (1969).
K. Shen and N. A. Kuebler, “Synthesis, reactions and photoelectron spectrum of 8,11-dimethylenepentacyclo[5.4.0.02,6.03,10.05,9]tridecane,” Tetrahedron Lett., No. 24, 2145–2148 (1973).
F. N. Stepanov, P. A. Krasutskii, and A. G. Yurchenko, “Reaction of 3,7-dimethylenebicyclo[3.3.1]nonane with perbenzoic and monoperphthalic acids,” Zh. Org. Khim.,8, No. 6, 1179–1183 (1972).
F. N. Stepanov, P. A. Krasutskii, and L. I. Rudenok, “Addition of hypohalites to 3,7-dimethylenebicyclo[3.3.1]nonane,” Zh. Org. Khim.,8, No. 12, 2616–2619 (1972).
L. A. Zosim and A. G. Yurchenko, “Hydrogenation of 3,7-dimethylenebicyclo[3.3.1]nonane in presence of tris(triphenylphosphine)rhodium chloride,” Vestn. Kiev. Politekh. Inst., Khim. Mashinostr. Tekhnol., No. 12, 11–12 (1975).
F. N. Stepanov, É. N. Martynova, L. A. Zosim, et al., “Hydrogenation of 3,7-dimethylenebicyclo[3.3.1]nonane on platinum catalyst,” Zh. Org. Khim.,7, No. 12, 2616–2619 (1971).
É. N. Martynova and A. G. Yurchenko, “Study of stepwise hydrogenation of 3,7-dimethylenebicyclo[3.3.1]nonane on platinum catalyst,” Khim. Tekhnol., No. 2, 3–5 (1973).
P. A. Krasutsky and M. Jones, “Reaction of diphenyl- and difluorocarbenes with 3, 7-dimethylenebicyclo[3.3.1]nonane,” J. Org. Chem.,45, No. 12, 2425–2429 (1980).
H. Stetter and J. Cartner, “Preparation and ring closure reaction of 3,7-dimethylenebicyclo[3.3.1]nonane,” Chem. Ber.,99, No. 3, 925–929 (1966).
A. G. Yurchenko, L. A. Zosim, N. L. Dovgan', and N. S. Verpovsky, “Free radical addition of carbon tetrahalides to the 3, 7-dimethylene[3.3.1]nonane,” Tetrahedron Lett., No. 52, 4843–4846 (1976).
P. A. Krasutskii, Yu. A. Serguchev, A. G. Yurchenko, and A. B. Khotkevich “Kinetics and mechanism of iodocyclization reaction of 3, 7-dimethylenebicyclo[3.3.1]nonane,” Teor. Éksp. Khim.,19, No. 2, 229–232 (1983).
A. G. Yurchenko, Z. N. Murzinova, and T. G. Fedorenko, “Problem of reactivity of bicyclic fragmentation products of adamantane derivatives,” Zh. Org. Khim.,10, No. 5, 1125 (1974).
J. G. Traynham and J. R. Olechovski, “Complexation of cyclic olefins with aqueous silver ion with molecular iodine,” J. Am. Chem. Soc.,81, No. 3, 571–574 (1959).
F. Freeman, “Possible criteria for distinguishing between cyclic and acyclic activated complexes in addition reactions,” Chem. Rev.,75, No. 4, 439–490 (1975).
G. B. Sergeev, V. V. Smirnov, and L. A. Tyurina, “Molecular mechanism of low temperature addition of halogens and hydrogen halides to olefins in liquid phase,” Zh. Fiz. Khim.,55, No. 9, 2209–2223 (1981).
V. I. Staninets and E. A. Shilov, “Addition reaction with intramolecular ring formation,” Usp. Khim.,40, No. 3, 481–512 (1971).
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Translated from Teoreticheskaya i Éksperiamental'naya Khimiya, Vol. 20, No. 6, pp. 732–737, November–December, 1984.
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Serguchev, Y.A., Khotkevich, A.B., Barabash, V.B. et al. Kinetics and reaction mechanism of iodination of diolefins with a bycyclo[3.3.1]nonane structure. Theor Exp Chem 20, 690–694 (1985). https://doi.org/10.1007/BF00568928
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DOI: https://doi.org/10.1007/BF00568928