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The Synthesis and Characterization of Diastereomeric 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-ones

Rohde, Laurence Nathaniel, Jr.
http://orcid.org/0000-0003-3908-5104
http://rave.ohiolink.edu/etdc/view?acc_num=ysu1533830233099792

Abstract Details

2018, Master of Science in Chemistry, Youngstown State University, Department of Chemistry.
The research herein describes the synthesis and stereochemical determination of chiral 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-ones in relatively good overall yields (64-80%). These products are five-membered ring derivatives of an FDA approved six-membered ring chemotherapeutic, cyclophosphamide. Products were obtained as a diastereomeric mixture through the synthetic use of enantiomerically pure chiral amino alcohols. Each product retains the bis(2-chloroethyl)amine moiety, which is well known for its potential chemotherapeutic use as an alkylating agent. Preliminary assignments of the absolute configuration at phosphorus were made based on literature references’ use of 31P NMR chemical shifts. These assignments are based on the syn/anti relationship of the chiral substituents present on the heterocycle with respect to the bis(2-chloroethyl)amine moiety. Single crystal X-ray diffraction (XRD) was then used to further support these trends by confirming the absolute configuration at phosphorus of diastereomerically pure crystalline products.
John Jackson, PhD (Advisor)
Douglas Genna, PhD (Committee Member)
Michael Serra, PhD (Committee Member)
191 p.
Chemistry; Organic Chemistry
Organic Chemistry; Organophosphorus; Nitrogen Mustard; Crystallography

Recommended Citations

Citations

  • Rohde, Jr., L. N. (2018). The Synthesis and Characterization of Diastereomeric 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-ones [Master's thesis, Youngstown State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1533830233099792

    APA Style (7th edition)

  • Rohde, Jr., Laurence. The Synthesis and Characterization of Diastereomeric 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-ones. 2018. Youngstown State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ysu1533830233099792.

    MLA Style (8th edition)

  • Rohde, Jr., Laurence. "The Synthesis and Characterization of Diastereomeric 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-ones." Master's thesis, Youngstown State University, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1533830233099792

    Chicago Manual of Style (17th edition)

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© 2018, all rights reserved.
This open access ETD is published by Youngstown State University and OhioLINK.