Skip to main content
SpringerLink
Log in

Stereoselective reaction between alkyl propiolates and phenols in the presence of sodium azide in tert-butyl alcohol

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Stereoselective reaction of various substituted phenols with alkyl propiolates in the presence of a catalytic amount of sodium azide in tert-butyl alcohol at reflux temperature leads to alkyl (Z)-3-phenoxy-2-propenoates in good yields.

Graphical abstract

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

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Yavari I, Adib M, Hojabri L (2002) Tetrahedron 58:6895

    Article  CAS  Google Scholar 

  2. Yavari I, Nourmohammadian F, Bijanzadeh HR (2002) Phosphorus Sulfur Silicon 177:1147

    Article  CAS  Google Scholar 

  3. Evans LA, Griffiths KE, Guthmann H (2002) Tetrahedron Lett 43:299

    Article  CAS  Google Scholar 

  4. Ramazani A, Kazemzadeh AR, Ahmadi E (2005) Phosphorus Sulfur Silicon 180:2373

    Article  Google Scholar 

  5. Ramazani A, Amini I, Massoudi A (2006) Phosphorus Sulfur Silicon 181:2373

    Article  CAS  Google Scholar 

  6. Yavari I, Anary-Abbasinejad M, Hossaini Z (2003) Org Biomol Chem 1:560

    Article  CAS  Google Scholar 

  7. Nair V, Deepthi A (2006) Tetrahedron Lett 47:2037

    Article  CAS  Google Scholar 

  8. Yavari I, Djahaniani H, Nasiri F (2003) Tetrahedron 59:9409

    Article  CAS  Google Scholar 

  9. Yavari I, Alizadeh A, Anary-Abbasinejad M, Hossaini Z (2003) Tetrahedron 59:1289

    Article  CAS  Google Scholar 

  10. Fan MJ, Li GQ, Liang YM (2006) Tetrahedron 62:6782

    Article  CAS  Google Scholar 

  11. Stoermer MJ, Fairlie DP (1995) Aust J Chem 48:677

    Article  CAS  Google Scholar 

  12. Matteson DS, Maliakal D, Fabry-Asztalos L (2008) J Organomet Chem 693:2258

    Article  CAS  Google Scholar 

  13. Tiecco M, Testaferri L, Santi C, Tomassini C, Santoro S, Marini F, Bagnoli L, Temperini A (2007) Tetrahedron 63:12373

    Article  CAS  Google Scholar 

  14. Lakshmi Kantam M, Swarna Jaya V, Sreedhar B, Mohan Rao M, Choudary BM (2006) J Mol Cat A Chem 256:273

    Article  Google Scholar 

  15. Yadav JS, Subba Reddy BV, Madhusudhan Reddy G, Narasimha Chary D (2007) Tetrahedron Lett 48:8773

    Article  CAS  Google Scholar 

  16. Chafin A, Irvin DJ, Mason MH, Mason SL (2008) Tetrahedron Lett 49:3823

    Article  CAS  Google Scholar 

  17. Yavari I, Souri S, Sirouspour M, Djahaniani H, Nasiri F (2005) Synthesis 1761

  18. Fan MJ, Li GQ, Li LH, Yang SD, Liang YM (2006) Synthesis 2286

  19. Ramachandran PV, Rudd MT, Reddy MVR (2005) Tetrahedron Lett 46:2547

    Article  CAS  Google Scholar 

  20. Nasiri F, Atashkar B (2008) Monatsh Chem 139:1223

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Kurdistan, P.O. Box 66315-416, Sanandaj, Iran

    Farough Nasiri & Davood Malakutikhah

Authors
  1. Farough Nasiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Davood Malakutikhah
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Farough Nasiri.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nasiri, F., Malakutikhah, D. Stereoselective reaction between alkyl propiolates and phenols in the presence of sodium azide in tert-butyl alcohol. Monatsh Chem 142, 807–812 (2011). https://doi.org/10.1007/s00706-011-0514-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0514-6

Keywords

Search

Navigation