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Youngstown State University

1. Rizzo, Lee A. Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates.

Degree: MSin Chemistry, Department of Chemistry, 2013, Youngstown State University

A new method for the synthesis of bis (2,2,2- trifluoroethyl) (Z)-vinyl phosphonates from bis (2,2,2-trifluoroethyl) 1-alkynyl phosphonates is described. 1-Alkynyl phosphonates, in the presence of Lindlar's catalyst, trifluoroethanol and H2 (g), are used to prepare the corresponding vinylphosphonates via a semireductive synthetic approach. With the starting materials in hand, specifically the 1-alkynylphophonates, which were synthesized using bis(2,2,2-trifluoroethyl)phosphorochloridate and the commercially available 1-alkynes, the obtaining of the desired target was accomplished. The semireduction of the triple bond was successful using Lindlar's catalyst in the presence of quinoline with 2,2,2-trifluoroethanol as reaction solvent. Additionally, a modified approach to this synthesis is explored such that only the kinetic (<i>Z</i>) isomer is formed. Advisors/Committee Members: Jackson, John (Advisor).

Subjects/Keywords: Agricultural Chemicals; Chemistry; Organic Chemistry; Pharmaceuticals; vinyl phosphonates; hydrogenation; semi-reduction; lindlar catalyst

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APA (6th Edition):

Rizzo, L. A. (2013). Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates. (Masters Thesis). Youngstown State University. Retrieved from http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849

Chicago Manual of Style (16th Edition):

Rizzo, Lee A. “Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates.” 2013. Masters Thesis, Youngstown State University. Accessed August 06, 2020. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849.

MLA Handbook (7th Edition):

Rizzo, Lee A. “Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates.” 2013. Web. 06 Aug 2020.

Vancouver:

Rizzo LA. Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates. [Internet] [Masters thesis]. Youngstown State University; 2013. [cited 2020 Aug 06]. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849.

Council of Science Editors:

Rizzo LA. Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates. [Masters Thesis]. Youngstown State University; 2013. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=ysu1380022849

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