Abstract
We have studied the kinetics of catalytic iodination of acetylene to form trans-1,2-diiodoethylene in the system PdII-NaI-I2-MeOH at 55 °C. The results obtained allow us to hypothesize that the reaction includes a step of iodopalladation of acetylene with intermediate formation of an σ-iodovinyl derivative of palladium, the decomposition of which by reductive elimination yields the end product and regenerates the catalyst.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
R. C. Larock and W. W. Leong, Comprehensive Organic Synthesis, B. M. Trost and I. Fleming (eds.), Pergamon Press, Oxford (1991), Vol. 4, p. 269.
J.-E. Backvall, Y. I. M. Nilsson, and R. G. P. Gatti, Organometallics, 14, 4242–4246 (1995).
Z. Wang and X. Lu, J. Org. Chem., 61, 2254–2255 (1996).
Y. Kataoka, O. Matsumoto, M. Ohashi, et al., Chem. Lett., 1283–1284 (1994).
S. Ma and X. Lu, J. Org. Chem., 58, No.5, 1245–1250 (1993).
V. P. Ananikov, S. A. Mitchenko, and I. P. Beletskaya, Zh. Org. Khim., 38, No.5, 672 (2002).
S. A. Mitchenko and A. A. Shubin, Organometallic Derivatives of Platinum Acido Complexes: Synthesis, Reactivity, and Design of Catalytic Reactions [in Russian], DonGUET, Donetsk (2004).
E. S. Rudakov, Reactions of Alkanes with Oxidants, Metal Complexes, and Radicals in Solutions [in Russian], Nauk. Dumka, Kiev (1985), pp. 47–62.
V. V. Strelets, S. V. Kukharenko, G. L. Soloveichik, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1484 (1985).
R. N. Goldberg and L. G. Hepler, Chem. Rev., 68, No.2, 229–252 (1968).
Yu. Yu. Lur'e, Analytical Chemistry Handbook [in Russian], Khimiya, Moscow (1971).
F. R. Hartley, The Chemistry of Platinum and Palladium, Wiley, New York/Toronto (1973).
R. A. Hollins and M. P. A. Campos, J. Org. Chem., 44, 3931 (1979).
R. A. Gossage, A. D. Ryabov, A. L. Spek, et al., J. Am. Chem. Soc., 121, No.11, 2488 (1999).
J. Collman, L. Higedas, J. Norton, and R. Finke, Principles and Applications of Organotransition Metal Chemistry [Russian translation], Mir, Moscow (1989), Pt. 1, p. 402.
Author information
Authors and Affiliations
Additional information
__________
Translated from Teoreticheskaya i Eksperimental'naya Khimiya, Vol. 41, No. 5, pp. 296–301, September–October, 2005.
Rights and permissions
About this article
Cite this article
Mitchenko, S.A., Strelets, V.V. & Mitchenko, E.S. Catalytic Iodination of Acetylene in the Iodopalladate(II)-I−-I2-MeOH System. Theor Exp Chem 41, 310–317 (2005). https://doi.org/10.1007/s11237-005-0057-1
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11237-005-0057-1