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Carbon-carbon bond formation and annulation reactions using trimethyl and triethyl orthoformates

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Abstract

Synthetic utility of trimethyl and triethyl orthoformates for carbon-carbon bond formation is briefly surveyed, particularly in relation to dialkoxymethylation, carbonyl transposition-homologation, and cycloalkenone annulation reactions recently reported from the authors’ and other laboratories. The complex mechanisms involved in the one-step and two-step annulations of rigid β,γ- and γ, δ-unsaturated ketones have been discussed.

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References

  • Becket G J P, Ellis G P and Trindade M I 1978aJ. Chem. Res. (S) 47

  • Becket G J P, Ellis G P and Trindade M I 1978bJ. Chem. Res. (M) 865

  • Casnati G, Grisafulli M and Ricca A 1965Tetrahedron Lett. 243

  • Chakraborti R, Deb S and Ghatak U R 1985aJ. Indian Chem. Soc. 42 883

    Google Scholar 

  • Chakraborti R, Ranu B C and Ghatak U R 1985bJ. Org. Chem. 50 5268

    Article  CAS  Google Scholar 

  • Chakraborti R, Ranu B C and Ghatak U R 1987Synth. Commun. 17 1539

    Article  CAS  Google Scholar 

  • Claisen L 1893Chem. Ber. 26 2729

    Article  Google Scholar 

  • Dasgupta R and Ghatak U R 1985Tetrahedron Lett. 26 1581

    Article  CAS  Google Scholar 

  • Dasgupta R, Ranu B C and Ghatak U R 1983Indian J. Chem. 22B 619

    CAS  Google Scholar 

  • Dewelfe R H 1970Carboxylic ortho acid derivatives (New York and London: Academic Press) p. 223

    Google Scholar 

  • Dorofeenko G N and Mezheritskii V V 1968J. Org. Chem. 4 1260

    Google Scholar 

  • Dorofeenko G N and Tkachenko V V 1972Chem. Heterocycl. Comp. 8 935

    Article  Google Scholar 

  • Dusza J P, Joseph J P and Bernstein S 1964J. Am. Chem. Soc. 86 3908

    Article  CAS  Google Scholar 

  • Fieser M and Fieser L 1967Reagents for organic synthesis (New York: Wiley-Interscience) p. 1204

    Google Scholar 

  • Ghatak U R, Sanyal B, Ghosh S, Sarkar M, Raju M S and Wenkert E 1980J. Org. Chem. 45 1081

    Article  CAS  Google Scholar 

  • Ghosh S 1978Synthetic studies in condensed cyclic systems Ph.D. dissertation, University of Calcutta

  • Gross H, Rieche A and Matthey G 1963Chem. Ber. 96 308

    Article  CAS  Google Scholar 

  • Hafner K, Peleter H and Schneider J 1961Liebigs Ann. Chem. 650 62

    Article  CAS  Google Scholar 

  • Howk B W and Sauer J C 1958J. Am. Chem. Soc. 80 4607

    Article  CAS  Google Scholar 

  • Howk B W and Sauer J C 1963Organic Synth. Coll. Vol. 4 801

    Google Scholar 

  • Kirby E C and Raid D H 1961J. Chem. Soc. 1724

  • Lombert S D, Nemery I, Roekens B, Carretero J C, Kimmel T and Ghosez L 1986Tetrahedron Lett. 275099

    Article  Google Scholar 

  • Miller B 1981J. Org. Chem. 46 2795

    Article  CAS  Google Scholar 

  • Mock W L and Tsou H R 1981J. Org. Chem. 46 2557

    Article  CAS  Google Scholar 

  • Mukaiyama T and Hayashi M 1974Chem. Lett. 15

  • Perron F and Albizati K F 1987J. Org. Chem. 52 4130

    Article  Google Scholar 

  • Perst H 1971Oxonium ions in organic chemistry (London: Verlag Chemie, Academic Press)

    Google Scholar 

  • Pettit G R, Knight J C and Herald C L 1970J. Org. Chem. 35 1593

    Google Scholar 

  • Ranu B C, Chakraborti R and Ghatak U R 1988J. Chem. Soc., Perkin Trans. 1 (in press)

  • Sathe V R and Venkatraman K 1949Curr. Sci. 18 373

    CAS  Google Scholar 

  • Schonberg A and Praefcke K 1964Tetrahedron Lett. 2043

  • Schonberg A and Praefcke K 1966Chem. Ber. 99 196

    Article  Google Scholar 

  • Schonberg A, Praefcke K and Kohtz J 1966Chem. Ber. 99 2433

    Article  Google Scholar 

  • Suzuki M, Kawagishi T and Noyori R 1981Tetrahedron Lett. 22 1809

    Article  CAS  Google Scholar 

  • Suzuki M, Yamagisawa A and Noyori R 1982Tetrahedron Lett. 23 3395

    Article  Google Scholar 

  • Takazawa O and Mukaiyama T 1982Chem. Lett. 1307

  • Treibe W 1967Tetrahedron Lett. 4707

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Authors and Affiliations

  1. Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, 700032, Calcutta, India

    Subrata Ghosh & Usha Ranjan Ghatak

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  1. Subrata Ghosh
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  2. Usha Ranjan Ghatak
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Ghosh, S., Ghatak, U.R. Carbon-carbon bond formation and annulation reactions using trimethyl and triethyl orthoformates. Proc. Indian Acad. Sci. (Chem. Sci.) 100, 235–252 (1988). https://doi.org/10.1007/BF02839451

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