Skip to main content
SpringerLink
Log in

Reactions of 3-acycloxysulfolanes with nucleophilic reagents

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In contrast to alkyl esters of carboxylic acids, 3-acyloxysulfolanes on reaction with nucleophilic reagents readily split out a carboxylic acid to give 2-sulfolene, which then reacts with compounds containing a labile hydrogen atom. On the basis of data on the kinetics of alkaline hydrolysis of benzoates, a scheme for elimination of the acid that includes the intermediate formation of a transition state of the E1CB type is proposed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. L. F. Lur'e, T. É. Bezmenova, T. I. Piskunova, and T. N. Arkhinova, Tekstil'u. Prom., No. 12, 59 (1973).

    Google Scholar 

  2. L. K. Brice, W. M. Chang, J. E. Smith, and S. M. Sullivan, J. Phys. Chem., 71, 2814 (1967).

    Google Scholar 

  3. C. S. Argyle, S. C. Gaadby, K. G. Mason, R. A. Reed, M. A. Smith, and E. S. Stern, J. Chem. Soc., 2156 (1967).

  4. R. C. Krug and D. Boswell, J. Org. Chem., 27, 95 (1962).

    Google Scholar 

  5. T. É. Bezmenova, A. F. Rekasheva, T. S. Lutsii, and R. A. Dorofeeva, Khim. Geterotsikl. Soedin., 1200 (1974).

  6. L. R. Fedor, J. Amer. Chem. Soc., 91, 908 (1969).

    Google Scholar 

  7. T. O. Pyussa, V. M. Nummert (Maremyae), and V. A. Pal'm, Reakts. Sposobnost' Organ. Soedin., 9, No. 3(33), 697 (1972).

    Google Scholar 

  8. T. O. Pyussa, V. M. Nummert (Maremyaé), and V. A. Pal'm, Reakts. Sposobnost' Organ. Soedin., 9, No. 3(33), 971 (1972).

    Google Scholar 

  9. K. D. Riche and U. F. Sedger, in: Modern Problems of Physical Organic Chemistry [Russian translation], Mir, Moscow (1967), p. 498.

    Google Scholar 

  10. R. C. Cavestri and L. R. Fedor, J. Amer. Chem. Soc., 92, 4610 (1970).

    Google Scholar 

  11. D. V. Banthorpe, Elimination Reactions, Vol., 4, Amsterdam (1963), p. 78.

    Google Scholar 

  12. C. Concilio and A. Bongini, Ann. Chim. (Rome), 56, 417 (1966).

    Google Scholar 

  13. N. V. Hayes and G. E. K. Branch, J. Amer. Chem. Soc., 65, 1555 (1943).

    Google Scholar 

  14. E. de Roy Van Zuydewijn, Rec. Trav. Chim., 56, 1042 (1937).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of the Chemistry of High-Molecular-Weight Compounds, Academy of Sciences of the Ukrainian SSR, Kiev

    T. É. Bezmenova, T. S. Lutsii, A. F. Rekasheva & Yu. N. Usenko

Authors
  1. T. É. Bezmenova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. S. Lutsii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. F. Rekasheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu. N. Usenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

L. S. Lur'e participated in the experimental work.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1060–1066, August, 1975.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bezmenova, T.É., Lutsii, T.S., Rekasheva, A.F. et al. Reactions of 3-acycloxysulfolanes with nucleophilic reagents. Chem Heterocycl Compd 11, 925–930 (1975). https://doi.org/10.1007/BF00470492

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00470492

Keywords

Search

Navigation