Reactions of lithium alkylalkenylamides.
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| Other Authors: | , , |
| Format: | Thesis Book |
| Language: | English |
| Published: |
1984.
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| Subjects: | |
| Online Access: | Link to ProQuest Copy Link to OAKTrust copy |
| Abstract: | The reactions of three lithium dialkylamides derived from N-alkyl-2-allylcyclohexylamine with several substrates which were potential one-electron acceptors were studied. These substrates were benzophenone, (E)-2-tert-butyl-3-phenyloxaziridine (4), and thianthrene (+1 radical cation) perchlorate (68). The structure of the amides was designed so that they could undergo rearrangement if transfer of one electron to the substrate occurred. The amides reacted with benzophenone (in tetrahydrofuran) to afford benzhydrol and the corresponding imines. The absence of rearranged products suggests that initial single electron transfer (SET) is not the major mechanistic pathway involved. On the other hand, a -hydride transfer mechanism would explain better the results obtained. (E)-2-tert-Butyl-3-phenyloxaziridine (4) underwent reduction to N-tert-butylbenzaldimine (6) and, to a small extent, isomerization to N-tert-butylbenzamide (5). This reaction was found to ionvolve single electron transfer from the amides to the oxaziridine, as evidenced by the presence of rearrangement products. Thianthrene (+1 radical cation) perchlorate (68) was reduced to thianthrene (69) by 33a-c, though no rearrangement products (36a-c) were observed in this case. |
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| Item Description: | "Major subject: Chemistry." Typescript (photocopy). Vita. |
| Physical Description: | x, 94 leaves : illustrations ; 29 cm |
| Bibliography: | Includes bibliographical references (leaves 85-93). |