Photochemical rearrangements of substituted thiochromanone sulfoxides
The photochemical behavior of a number of substituted derivatives of thiochroman-4-one 1-oxide has been examined. In contrast to the analogous sulfones these sulfoxides undergo a variety of photochemical rearrangements. At least three distinct pathways have been recognized; β-hydrogen abstraction or...
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| Veröffentlicht in: | Canadian journal of chemistry 1976-02, Vol.54 (3), p.455-470 |
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| container_end_page | 470 |
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| container_issue | 3 |
| container_start_page | 455 |
| container_title | Canadian journal of chemistry |
| container_volume | 54 |
| creator | Still, I. W. J Arora, P. C Chauhan, M. S Kwan, M.-H Thomas, M. T |
| description | The photochemical behavior of a number of substituted derivatives of thiochroman-4-one 1-oxide has been examined. In contrast to the analogous sulfones these sulfoxides undergo a variety of photochemical rearrangements. At least three distinct pathways have been recognized; β-hydrogen abstraction or rearrangement to cyclic sulfenates, which then undergo further reaction by homolysis of the SO bond, appearing to be particularly favorable processes. In a small number of examples, photochemical deoxygenation is observed as a competing reaction. Mechanisms which attempt to account for the influence of structural variations on the particular pathway followed have been proposed. |
| doi_str_mv | 10.1139/v76-062 |
| format | Article |
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W. J ; Arora, P. C ; Chauhan, M. S ; Kwan, M.-H ; Thomas, M. T</creator><creatorcontrib>Still, I. W. J ; Arora, P. C ; Chauhan, M. S ; Kwan, M.-H ; Thomas, M. T</creatorcontrib><description>The photochemical behavior of a number of substituted derivatives of thiochroman-4-one 1-oxide has been examined. In contrast to the analogous sulfones these sulfoxides undergo a variety of photochemical rearrangements. At least three distinct pathways have been recognized; β-hydrogen abstraction or rearrangement to cyclic sulfenates, which then undergo further reaction by homolysis of the SO bond, appearing to be particularly favorable processes. In a small number of examples, photochemical deoxygenation is observed as a competing reaction. 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At least three distinct pathways have been recognized; β-hydrogen abstraction or rearrangement to cyclic sulfenates, which then undergo further reaction by homolysis of the SO bond, appearing to be particularly favorable processes. In a small number of examples, photochemical deoxygenation is observed as a competing reaction. Mechanisms which attempt to account for the influence of structural variations on the particular pathway followed have been proposed.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v76-062</doi><tpages>16</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Canadian journal of chemistry, 1976-02, Vol.54 (3), p.455-470 |
| issn | 0008-4042 1480-3291 |
| language | eng |
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| source | NRC Research Press; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| title | Photochemical rearrangements of substituted thiochromanone sulfoxides |
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