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Development of a Safe and Efficient Alkyl Azide Synthesis using Arylsulfonyl Azide

Okumu, Antony A.
http://rave.ohiolink.edu/etdc/view?acc_num=ysu1290962115

Abstract Details

2010, Master of Science in Chemistry, Youngstown State University, Department of Chemistry.
Sodium azide has traditionally been used as the source of azide anion for the synthesis of alkyl azides. Besides difficulties with solubility, sodium azide is toxic, can be absorbed through the skin, and forms potentially explosive compounds with H2O, Brønsted acids, CH2Cl2, and CHCl3. To avoid these dangers, a new azide transfer reagent was developed from the reaction of 4-acetamidobenzenesulfonyl azide (p-ABSA) and 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU). It is much safer than sodium azide and was used for the synthesis of alkyl and acyl azides. Alkyl azides thus obtained were employed in an attempted in situ generation of 1,2,3-triazoles, which are aromatic five-membered ring heterocycles having two carbon atoms and three nitrogen atoms, and are biologically important. A known one-pot procedure for 1,2,3-triazole synthesis, described by Fokin and colleagues, was repeated and the formation and ease of isolation of the triazole products was compared with the new chemistry described herein.
Peter Norris, PhD (Advisor)
John Jackson, PhD (Committee Member)
Nina Stourman, PhD (Committee Member)
115 p.
Chemistry; Experiments; Occupational Safety; Organic Chemistry
p-ABSA DBU organic soluble salt; alkyl azide synthesis; 1,2,3-triazole attempted synthesis; suitable solvent

Recommended Citations

Citations

  • Okumu, A. A. (2010). Development of a Safe and Efficient Alkyl Azide Synthesis using Arylsulfonyl Azide [Master's thesis, Youngstown State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1290962115

    APA Style (7th edition)

  • Okumu, Antony. Development of a Safe and Efficient Alkyl Azide Synthesis using Arylsulfonyl Azide. 2010. Youngstown State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ysu1290962115.

    MLA Style (8th edition)

  • Okumu, Antony. "Development of a Safe and Efficient Alkyl Azide Synthesis using Arylsulfonyl Azide." Master's thesis, Youngstown State University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1290962115

    Chicago Manual of Style (17th edition)

ysu1290962115
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© 2010, all rights reserved.
This open access ETD is published by Youngstown State University and OhioLINK.