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Role of orbital symmetry in transition metal promoted ring opening reactions of methylenecyclopropanes and cyclobutenes

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Abstract

Transition metals catalyse a variety of organic reactions, of which the ring opening of strained ring organic molecules generated a lot of interest. Theoreticians predicted a metal orbital catalysed pathway, which involved concerted bond breaking and bond forming. On the other hand experimentalists were able to show that the reaction was not proceeding through a concerted pathway by intercepting the intermediates involved. There remained, however, two ring systems methylenecyclopropanes and cyclobutenes—whose reactions with metal complexes seemed to be of a concerted nature. An analysis of the reactions of different metal complexes with these ring systems and the theoretical predictions provide a rationale for understanding these reactions.

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References

  • Barnes S G and Green M 1980J. Chem. Soc. Chem. Commun. 267

  • Billups W E, Lin L P and Baker B A 1972Angew. Chem. Int. Ed. Engl. 11 637

    Article  CAS  Google Scholar 

  • Cassar L and Halpern J 1971J. Chem. Soc. Chem. Commun. 1082

  • Dewar M J S 1971Angew. Chem. Int. Ed. Engl. 10 761

    Article  CAS  Google Scholar 

  • Fukui K and Inagaki S 1975J. Am. Chem. Soc. 97 4445

    Article  CAS  Google Scholar 

  • Gassman P G and Reitz R R 1973J. Organometal. Chem. 152 C51

    Article  Google Scholar 

  • Graham C R, Scholes G and Brookhart M S 1977J. Am. Chem. Soc. 99 1180

    Article  CAS  Google Scholar 

  • Green M and Hughes R P 1976J. Chem. Soc. Dalton Trans. 1890

  • Grimme W and Schneider E 1977Angew. Chem. Int. Ed. Engl. 16 717

    Article  Google Scholar 

  • Hughes R P, Hunton D E and Schumann K 1979J. Organometal. Chem. 169 C37

    Article  CAS  Google Scholar 

  • Mango F D and Schachtschneider 1965J. Am. Chem. Soc. 87 2045

    Article  Google Scholar 

  • Mango F D and Schachtschneider 1971J. Am. Chem. Soc. 93 1123

    Article  CAS  Google Scholar 

  • Noyori R and Takaya H 1969J. Chem. Soc. Chem. Commun. 525

  • Noyori R Nishimura T and Takaya H 1969J. Chem. Soc. Chem. Commun. 89

  • Pearson R G 1976Chem. Br. 12 60

    Google Scholar 

  • Pettit R, Sugahara H, Wristers J and Merck W 1969Disc. Farad. Soc. 47 71

    Article  Google Scholar 

  • Pinhas A R 1980 Ph.D Dissertation, Cornell University

  • Pinhas A R and Carpenter B K 1980aJ. Chem. Soc. Chem. Commun. 15

  • Pinhas A R and Carpenter B K 1980bJ. Chem. Soc. Chem. Commun. 17

  • Pinhas A R, Samuelson A G, Risemberd R, Arnold E. V., Clardy J and Carpenter B K 1981J. Am. Chem. Soc. 103 1168

    Article  Google Scholar 

  • Samuelson A G 1983 Ph.D Dissertation, Cornell University

  • Samuelson A G and Carpenter B K 1981J. Chem. Soc. Chem. Commun. 354

  • Scholes G, Graham C R and Brookhart M S 1974J. Am. Chem. Soc. 96 5665

    Article  CAS  Google Scholar 

  • Shvo and Hazum E 1975J. Chem. Soc. Chem. Commun. 829

  • Skell P S and Sandier S R 1958J. Am. Chem. Soc. 80 2024

    Article  CAS  Google Scholar 

  • Slegir W, Case R, Mc Kennis J S and Pettit R 1974J. Am. Chem. Soc. 96 287

    Article  Google Scholar 

  • Whitesides T H, Slaven R W and Calabrese J C 1974Inorg. Chem. 13 1895

    Article  CAS  Google Scholar 

  • Woodward R B and Hoffman R 1971Conservation of orbital symmetry (Verlog Chemie)

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  1. Department of Inorganic and Physical Chemistry, Indian Institute of Science, S60012, Bangalore, India

    Ashoka G. Samuelson

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  1. Ashoka G. Samuelson
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Samuelson, A.G. Role of orbital symmetry in transition metal promoted ring opening reactions of methylenecyclopropanes and cyclobutenes. Proc. Indian Acad. Sci. (Chem. Sci.) 93, 729–739 (1984). https://doi.org/10.1007/BF02863289

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