Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V. Reactions of 2-(α-Chloroalkyl)thiiranes with organolithium compounds
2-(α-Haloalkyl)thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro- and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)- and (Z)-1-phenylsulfanylbut-2-enes, respe...
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| Veröffentlicht in: | Russian journal of organic chemistry 2010-12, Vol.46 (12), p.1822-1825 |
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| container_issue | 12 |
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| container_title | Russian journal of organic chemistry |
| container_volume | 46 |
| creator | Tomashevskii, A. A Sokolov, V. V Potekhin, A. A |
| description | 2-(α-Haloalkyl)thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro- and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)- and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2-dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed. |
| doi_str_mv | 10.1134/S1070428010120080 |
| format | Article |
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The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp9kEFOwzAQRSMEEqVwAFZ4CYuUmdh1bHaoAopUCYlStpFxnMQljSs7EeoZOA0X4UykKjsqVvOlP-9r5kfROcIIkbLrOUIKLBGAgAmAgINogBxETKmkh73u7XjrH0cnISwBgCGjg-jz2SjdWtcE4gqSxJffX_FU1U7V75v6qq2s9aoxgXzYtiJNp2vj1pWtrSbeqNI0bbghryOyJ2VS1c7vz3G-VI2re2m7FdFutXZdk4fT6KhQdTBnv3MYLe7vXibTePb08Di5ncU64ayNRSH5WHBeYP8xL9Q4TwVjwHQuDS-MEFxIxcEgGDlGhbmS6VtKmeE60VIrOoxwl6u9C8GbIlt7u1J-kyFk2zazP232TLJjQr_blMZnS9f5pj_zX-hiBxXKZar0NmSLeQJIASVDEEh_AD0lguE</recordid><startdate>20101201</startdate><enddate>20101201</enddate><creator>Tomashevskii, A. A</creator><creator>Sokolov, V. V</creator><creator>Potekhin, A. 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The reactions of diastereoisomeric erythro- and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)- and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2-dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed.</abstract><cop>Dordrecht</cop><pub>Dordrecht : SP MAIK Nauka/Interperiodica</pub><doi>10.1134/S1070428010120080</doi><tpages>4</tpages></addata></record> |
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| title | Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V. Reactions of 2-(α-Chloroalkyl)thiiranes with organolithium compounds |
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