Synthesis of CF3-Containing Sulfur Heterocycles. The First Stable 2-Thietanol Derivative
The reaction of α,β-unsaturated CF3-containing ketones R1R2CCHCOCF3 1−4 with ammonium hydrosulfide was investigated. The structure of the enones was shown to influence the reaction path, and the corresponding six-membered sulfur heterocycles bearing trifluoromethyl groups, 5−8, or mercaptan, 9, wer...
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| Veröffentlicht in: | Journal of organic chemistry 1996-03, Vol.61 (6), p.1986-1989 |
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| container_end_page | 1989 |
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| container_issue | 6 |
| container_start_page | 1986 |
| container_title | Journal of organic chemistry |
| container_volume | 61 |
| creator | Sanin, Andrei V Nenajdenko, Valentine G Kuz'min, Vladimir S Balenkova, Elizabeth S |
| description | The reaction of α,β-unsaturated CF3-containing ketones R1R2CCHCOCF3 1−4 with ammonium hydrosulfide was investigated. The structure of the enones was shown to influence the reaction path, and the corresponding six-membered sulfur heterocycles bearing trifluoromethyl groups, 5−8, or mercaptan, 9, were obtained. The reaction of 3-adamantylidene-1,1,1-trifluoropropan-2-one, 3, results in the corresponding four-membered heterocycle 8, which has a stable 2-thietanol fragment. The oxidation of sulfides 5−8 by hydrogen peroxide yields sulfones 10−12 or 1,3-sultine 13 (in the case of 8). Product stereochemistry and reaction mechanism are discussed. |
| doi_str_mv | 10.1021/jo951351c |
| format | Article |
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The First Stable 2-Thietanol Derivative</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The reaction of α,β-unsaturated CF3-containing ketones R1R2CCHCOCF3 1−4 with ammonium hydrosulfide was investigated. The structure of the enones was shown to influence the reaction path, and the corresponding six-membered sulfur heterocycles bearing trifluoromethyl groups, 5−8, or mercaptan, 9, were obtained. The reaction of 3-adamantylidene-1,1,1-trifluoropropan-2-one, 3, results in the corresponding four-membered heterocycle 8, which has a stable 2-thietanol fragment. The oxidation of sulfides 5−8 by hydrogen peroxide yields sulfones 10−12 or 1,3-sultine 13 (in the case of 8). 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The First Stable 2-Thietanol Derivative</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1996-03-22</date><risdate>1996</risdate><volume>61</volume><issue>6</issue><spage>1986</spage><epage>1989</epage><pages>1986-1989</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The reaction of α,β-unsaturated CF3-containing ketones R1R2CCHCOCF3 1−4 with ammonium hydrosulfide was investigated. The structure of the enones was shown to influence the reaction path, and the corresponding six-membered sulfur heterocycles bearing trifluoromethyl groups, 5−8, or mercaptan, 9, were obtained. The reaction of 3-adamantylidene-1,1,1-trifluoropropan-2-one, 3, results in the corresponding four-membered heterocycle 8, which has a stable 2-thietanol fragment. The oxidation of sulfides 5−8 by hydrogen peroxide yields sulfones 10−12 or 1,3-sultine 13 (in the case of 8). Product stereochemistry and reaction mechanism are discussed.</abstract><pub>American Chemical Society</pub><doi>10.1021/jo951351c</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 1996-03, Vol.61 (6), p.1986-1989 |
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| language | eng |
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| source | ACS Publications |
| title | Synthesis of CF3-Containing Sulfur Heterocycles. The First Stable 2-Thietanol Derivative |
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