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Mechanistic Investigation into the Formation of 5-Iodo-1,2,3-Triazole through NMR Assay

Title: Mechanistic Investigation into the Formation of 5-Iodo-1,2,3-Triazole through NMR Assay.
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Name(s): Okashah, Najeah, author
Department of Chemistry and Biochemistry
Type of Resource: text
Genre: Text
Issuance: serial
Date Issued: 2014
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: Research into the synthesis of 5-iodo-1,2,3-triazoles (iodotriazoles) has been the subject of recent work because of the potential iodotriazoles have in multicomponent synthesis. Previously proposed mechanisms for the formation of iodotriazoles suggested that the reaction proceeded through a copper(I) acetylide intermediate. This work follows up on a prior publication (Barsoum, D.N. et al. Synthesis 2013, 45(17), 2372-2386) and provides further insight into an alternative mechanism in which 1-iodoalkyne was confirmed as an intermediate for the synthesis of iodotriazoles. The majority of the investigations were carried out through real-time NMR monitoring of the reaction components. Using this assay the effect of each reactant component on the reaction was studied. Iodoalkyne formation and the rate of the cyclization of the iodotriazole were found to be highly dependent on the amount of base initially present. The formation of both iodoalkyne and iodotriazole depend on the ratio of copper(II) to the iodide source rather than being directly dependent on the amount of copper(II) initially present. With a higher ratio of LiI: Cu(ClO4)2.6H2O accelerating the reaction. The formation of the iodoalkyne intermediate was found be almost instantaneous. Iodoalkyne formation competes directly with the formation of the H-triazole, and it is this competition that determines the selectivity of the reaction.
Identifier: FSU_migr_uhm-0340 (IID)
Keywords: 1-iodoalkyne, 5-iodo-1, 2, 3-triazole, NMR, mechanism
Submitted Note: A Thesis submitted to the Department of Chemistry & Biochemistry in partial fulfillment of the requirements for graduation with Honors in the Major.
Degree Awarded: Spring Semester, 2014.
Date of Defense: April 22, 2014.
Subject(s): Chemistry, Organic
Persistent Link to This Record: http://purl.flvc.org/fsu/fd/FSU_migr_uhm-0340
Restrictions on Access: http://creativecommons.org/licenses/by/4.0/
Owner Institution: FSU
Is Part of Series: Honors Theses.

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Okashah, N. (2014). Mechanistic Investigation into the Formation of 5-Iodo-1,2,3-Triazole through NMR Assay. Retrieved from http://purl.flvc.org/fsu/fd/FSU_migr_uhm-0340