Skip to main content
Log in

A new synthesis of thiophenes and thiapyrans

Part V. 6:7-Benzothionaphthene and 9-chloronaphtho-(1′:8′-bc)-thiapyran

  • Published:
Proceedings of the Indian Academy of Sciences - Section A Aims and scope Submit manuscript

Summary

8-Chloro-1-thionaphthol, prepared fromperi-acid, was condensed with bromoacetaldehyde dimethyl acetal to give 8-chloro-1-naphthylω-dimethoxyethyl sulphide (IV). Ring-closure of (IV) gave 3′-chlorobenzo-(1′:2′, 6:7)-thionaphthene (V), which on dechlorination gave 6:7-benzothionaphthene (II). The cyclization product fromα-naphthylω-dimethoxyethyl sulphide (I) reported in the previous communication being different from (II) is therefore naphtho-(1′:8′-bc)-thiapyran (III).

9-Chloronaphtho-(1′:8′-bc)-thiapyran (VII) was prepared from Tobias acid in a manner similar to (V), but dechlorination of (VII) to (III) could not be carried out due to the low yields of (VII) in the cyclization of 2-chloro-1-naphthylω-dimethoxyethyl sulphide (VI).

The literature on the cyclization of certain relatedα-substituted naphthyl, naphthoxy and thionaphthoxy derivatives is discussed.

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

Access this article

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

References

  1. Szmuzkovicz and Modest..J. Am. Chem. Soc., 1950,72, 571.

    Article  Google Scholar 

  2. ..DRP., 230, 237.

  3. Johnson..Organic Reactions, 1944, Vol.II, p. 125 (John Wiley).

    Google Scholar 

  4. Inghamet al. ..J. Chem. Soc., 1931, 895.

  5. Ullmann..Ber., 1897,30, 1468.

    Google Scholar 

  6. Anand and VenkataramanProc. Ind. Acad. Sci., 1948,28A, 160.

    Google Scholar 

  7. Friedländer and WoroschzowAnnalen, 1912,388, 18.

    Google Scholar 

  8. Harley-Mason and MannJ. Chem. Soc., 1942, 404.

  9. Stoermer..Annalen, 1900,312, 310.

    Google Scholar 

  10. Tilak..Proc. Ind. Acad. Sci., 1950,32A, 390.

    Google Scholar 

  11. Dosser and Richter..J. Am. Chem. Soc., 1934,56, 1132.

    Article  Google Scholar 

  12. Harley-Mason and MannJ. Chem. Soc., 1942, 404.

Download references

Author information

Authors and Affiliations

Authors

Additional information

Communicated by Dr. K. Venkataraman,f.a.sc.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dikshit, V.K., Tilak, B.D. A new synthesis of thiophenes and thiapyrans. Proc. Indian Acad. Sci. (Math. Sci.) 33, 78 (1951). https://doi.org/10.1007/BF03172186

Download citation

  • Received:

  • DOI: https://doi.org/10.1007/BF03172186

Keywords

Navigation