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APPLYING A LATE-STAGE LAWESSON’S CYCLIZATION STRATEGY TOWARDS THE SYNTHESIS OF 1,3,4-THIADIAZOLE-2-CARBOXYLATE THIOESTERS

Sutherland, Ian Thor
http://orcid.org/0000-0002-4494-4594
http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1437100137

Abstract Details

2015, BS, Kent State University, College of Arts and Sciences / Department of Chemistry and Biochemistry.
1,3,4-thiadiazole-2-carboxylate thioesters are attractive moieties for inclusion in potentially ferroelectric liquid crystalline materials (possess a strong lateral dipole, small width, and a large bend angle between C2 and C5). The Late-Stage Lawesson's Cyclization strategy has proven extremely effective in preparing these materials. Cyclization of the appropriate 1,4,5-tricarbonyl precursors as the last step in the synthetic pathway has avoided rapid competing decarboxylation reactions, providing high yields and allowing a simple purification process. Three examples of liquid crystalline materials exhibiting wide SmC phases have been prepared.
Paul Sampson, Dr. (Advisor)
Alexander Seed, Dr. (Advisor)
79 p.
Chemical Engineering; Chemistry; Materials Science; Organic Chemistry
liquid crystal; liquid crystals, ferroelectric; smectic C; 1,3,4-thiadiazole; thiadiazole; thioester; Lawesson; Lawessons; tricarbonyl

Recommended Citations

Citations

  • Sutherland, I. T. (2015). APPLYING A LATE-STAGE LAWESSON’S CYCLIZATION STRATEGY TOWARDS THE SYNTHESIS OF 1,3,4-THIADIAZOLE-2-CARBOXYLATE THIOESTERS [Undergraduate thesis, Kent State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1437100137

    APA Style (7th edition)

  • Sutherland, Ian. APPLYING A LATE-STAGE LAWESSON’S CYCLIZATION STRATEGY TOWARDS THE SYNTHESIS OF 1,3,4-THIADIAZOLE-2-CARBOXYLATE THIOESTERS. 2015. Kent State University, Undergraduate thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1437100137.

    MLA Style (8th edition)

  • Sutherland, Ian. "APPLYING A LATE-STAGE LAWESSON’S CYCLIZATION STRATEGY TOWARDS THE SYNTHESIS OF 1,3,4-THIADIAZOLE-2-CARBOXYLATE THIOESTERS." Undergraduate thesis, Kent State University, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1437100137

    Chicago Manual of Style (17th edition)

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