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Chiral sulfur compounds. XXI. Addition of azide ion to ß-aryl-¿-phenylsulfinylacrylates

Journal Article


Abstract


  • The reaction of methyl β-aryl-α- phenylsulfinylacrylates (1) with sodium azide /acetic acid gives triazoles (6) while the reaction of (1) with sodium azide /hydrochloric acid gives β-azido esters (7a, b). Reaction of (7a) with 1, 8-diazabicyclo[5.4.0]undec-7-ene, and (7b) with triethylamine gave the corresponding triazoles (6a) and (6b), respectively. Thus the formation of triazoles from the reaction of acrylates with azide ion most likely involves Michael addition of azide ion followed by cyclization of an incipient β-azido α-anion. © 1993 ASEG.

Publication Date


  • 1993

Citation


  • Dong, Z., Hellmund, K. A., & Pyne, S. G. (1993). Chiral sulfur compounds. XXI. Addition of azide ion to ß-aryl-¿-phenylsulfinylacrylates. Australian Journal of Chemistry, 46(9), 1431-1436. doi:10.1071/CH9931431

Scopus Eid


  • 2-s2.0-33544471801

Web Of Science Accession Number


Start Page


  • 1431

End Page


  • 1436

Volume


  • 46

Issue


  • 9

Abstract


  • The reaction of methyl β-aryl-α- phenylsulfinylacrylates (1) with sodium azide /acetic acid gives triazoles (6) while the reaction of (1) with sodium azide /hydrochloric acid gives β-azido esters (7a, b). Reaction of (7a) with 1, 8-diazabicyclo[5.4.0]undec-7-ene, and (7b) with triethylamine gave the corresponding triazoles (6a) and (6b), respectively. Thus the formation of triazoles from the reaction of acrylates with azide ion most likely involves Michael addition of azide ion followed by cyclization of an incipient β-azido α-anion. © 1993 ASEG.

Publication Date


  • 1993

Citation


  • Dong, Z., Hellmund, K. A., & Pyne, S. G. (1993). Chiral sulfur compounds. XXI. Addition of azide ion to ß-aryl-¿-phenylsulfinylacrylates. Australian Journal of Chemistry, 46(9), 1431-1436. doi:10.1071/CH9931431

Scopus Eid


  • 2-s2.0-33544471801

Web Of Science Accession Number


Start Page


  • 1431

End Page


  • 1436

Volume


  • 46

Issue


  • 9