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A New Late-Stage Lawesson's Cyclization Strategy Towards the Synthesis of Aryl 1,3,4-Thiadiazole-2-Carboxylate Esters

Schmidt, Michael Joseph
http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1373911614

Abstract Details

2013, BS, Kent State University, College of Arts and Sciences / Department of Chemistry and Biochemistry.
1,3,4-Thiadiazole-2-carboxylate esters are attractive moieties for inclusion in potential ferroelectric liquid crystalline materials (strong later dipole, relatively small bend between C2 and C5, compact size, etc.). However, methods for preparing these materials (of which there are few) have proven difficult in the past due primarily to competition from decarboxylation reactions leading to large amounts of byproducts. Postponing the cyclization of appropriate 1,4,5-tricarbonyl precursors until the last step has proven effective, circumventing demanding experimental conditions and difficult purification processes. Three examples of liquid crystalline materials exhibiting wide SmC phases have been prepared using this method.
Paul Sampson, Dr. (Advisor)
Alexander Seed, Dr. (Advisor)
106 p.
Chemical Engineering; Chemistry; Materials Science
liquid crystal; liquid crystals; 1,3,4-thiadiazole; tricarbonyl; tricarbonyls; ferroelectric; Lawessons reagent; Lawessons; Lawesson; thiadiazole

Recommended Citations

Citations

  • Schmidt, M. J. (2013). A New Late-Stage Lawesson's Cyclization Strategy Towards the Synthesis of Aryl 1,3,4-Thiadiazole-2-Carboxylate Esters [Undergraduate thesis, Kent State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1373911614

    APA Style (7th edition)

  • Schmidt, Michael. A New Late-Stage Lawesson's Cyclization Strategy Towards the Synthesis of Aryl 1,3,4-Thiadiazole-2-Carboxylate Esters. 2013. Kent State University, Undergraduate thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1373911614.

    MLA Style (8th edition)

  • Schmidt, Michael. "A New Late-Stage Lawesson's Cyclization Strategy Towards the Synthesis of Aryl 1,3,4-Thiadiazole-2-Carboxylate Esters." Undergraduate thesis, Kent State University, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1373911614

    Chicago Manual of Style (17th edition)

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This open access ETD is published by Kent State University Honors College and OhioLINK.