Imino‐λ3‐iodane and Catalytic Amount of I2‐Mediated Synthesis of N‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement; European Journal of Organic Chemistry; Vol. 2020, iss. 41
| Parent link: | European Journal of Organic Chemistry Vol. 2020, iss. 41.— 2020.— [P. 6433-6439] |
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| Körperschaften: | , , |
| Weitere Verfasser: | , , , , , , |
| Zusammenfassung: | Title screen A facile metal‐free [2,3]‐sigmatropic rearrangement reaction of allyl sulfides via N‐sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino‐λ3‐iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N‐allylsulfenamide compounds in moderate to good yields. Several N‐allylsulfenamide structures have been confirmed by single‐crystal X‐ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino‐λ3‐iodane and the sulfur atom, resulting in the formation of N‐sulfilimine species, followed by [2,3]‐sigmatropic rearrangement to form the N‐allylsulfenamide. Режим доступа: по договору с организацией-держателем ресурса |
| Sprache: | Englisch |
| Veröffentlicht: |
2020
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| Schlagworte: | |
| Online-Zugang: | https://doi.org/10.1002/ejoc.202000961 |
| Format: | MixedMaterials Elektronisch Buchkapitel |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=662982 |
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| 200 | 1 | |a Imino‐λ3‐iodane and Catalytic Amount of I2‐Mediated Synthesis of N‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement |f C. L. Makitalo, A. Yoshimura, I. A. Mironova [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: 22 tit.] | ||
| 330 | |a A facile metal‐free [2,3]‐sigmatropic rearrangement reaction of allyl sulfides via N‐sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino‐λ3‐iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N‐allylsulfenamide compounds in moderate to good yields. Several N‐allylsulfenamide structures have been confirmed by single‐crystal X‐ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino‐λ3‐iodane and the sulfur atom, resulting in the formation of N‐sulfilimine species, followed by [2,3]‐sigmatropic rearrangement to form the N‐allylsulfenamide. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t European Journal of Organic Chemistry | ||
| 463 | |t Vol. 2020, iss. 41 |v [P. 6433-6439] |d 2020 | ||
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a труды учёных ТПУ | |
| 610 | 1 | |a hypervalent compounds | |
| 610 | 1 | |a iodine | |
| 610 | 1 | |a sigmatropic rearrangement | |
| 610 | 1 | |a sulfilimines | |
| 610 | 1 | |a synthetic methods | |
| 610 | 1 | |a гипервалентные связи | |
| 610 | 1 | |a иод | |
| 610 | 1 | |a синтетические методы | |
| 701 | 1 | |a Makitalo |b C. L. |g Cody | |
| 701 | 1 | |a Yoshimura |b A. |c chemical engineer |c Professor of Tomsk Polytechnic University |f 1981- |g Akira |3 (RuTPU)RU\TPU\pers\39852 |9 21126 | |
| 701 | 1 | |a Mironova |b I. A. |c chemist |c engineer of Tomsk Polytechnic University |f 1993- |g Irina Andreevna |3 (RuTPU)RU\TPU\pers\37474 |9 20361 | |
| 701 | 1 | |a Yusubova |b R. Ya. |c chemist |c Associate Professor of Tomsk Polytechnic University, candidate of chemical sciences |f 1964- |g Roza Yavidovna |3 (RuTPU)RU\TPU\pers\35462 |9 18659 | |
| 701 | 1 | |a Yusubov |b M. S. |c chemist |c Professor of Tomsk Polytechnic University, Doctor of chemical sciences |f 1961- |g Mekhman Suleiman-Ogly (Suleimanovich) |3 (RuTPU)RU\TPU\pers\31833 | |
| 701 | 1 | |a Zhdankin |b V. V. |c химик |c Professor of Tomsk Polytechnic University, Doctor of chemical sciences |f 1956- |g Viktor Vladimirovich |3 (RuTPU)RU\TPU\pers\35758 | |
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