Document Type

Thesis - Open Access

Award Date


Degree Name

Master of Science (MS)




The primary objective of the research outlined in Part One is to assign the stereochemistry of some phosphorus containing heterocycles. In order to avoid confusion over nomenclature, most of the compounds described in this thesis will be named as derivatives of the 1,3,2-dioxaphosphorinan ring. For compounds described in the Experimental section, the designation of cis and trans will be assigned according to the arrangement of the phosphoryl oxygen at position 2 in relation to the chloromethyl group at C-5. Axial (ax) and equatorial (eq) designations will also refer to the chloromethyl group at 5, unless otherwise stated. Thus, the axial chair conformer of trans-5-chloromethyl-5-methyl-2-oxo-2-(R4)-l,3,2-dioxaphosphorinan refers to (1). Most of the compounds described in the Experimental section will be referred to by Roman numerals as outlined in Table (1). The stereochemistry has been established for compounds (III), (IV), (VI), and (VII). However, the stereochemistry of compounds (VIII)-(XVII) and (V) is not known and therefore, the relationship of substituents at C-5 to P-2 as outlined in Table 1 is arbitrary. The reaction of (IV) with sodium phenoxide yielded a mixture of compounds which were found to be isomers of 5-chloromethyl-5-methyl-2-oxo-2phenoxy-1,3,2-dioxaphosphorinan. NMR signals at 0.96 δ and 1.28 δ were assigned to methyl groups. Chloromethyl groups were assigned to signals at 3.34 δ and 3.77 δ. It is assumed that the product is a mixture of two isomers. When this material was subjected to chromatographic analysis (see Experimental) two compounds were isolated; isomer A (mp 105) and isomer B (mp 136). The nmr spectrum of A included signals at 0.96 δ and 3.77 δ. Likewise, the spectrum of B indicated signals at 1.28 δ and 3.34 δ. Recombination of A and B gave a spectrum similar to the one obtained from the original mixture. The purpose of Part One is to define the stereochemistry of isomer A and isomer B. It should be noted, A is synonymous with (VIII) and B is synonymous with (IX).

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South Dakota State University