Unexpected Product of Allyl Hydroxylation During Ozone Degradation of N-Tosylate 2-(Cyclohex-1-en-1-yl)-6-methylaniline

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅或者付费存取

详细

During the ozonolysis of N-[(2-cyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide followed by the reduction of oxidation products with dimethyl sulfide, the expected ketoaldehyde—4-methyl-N-[2-methyl-6-(6-oxohexanoyl)phenyl]benzenesulfonamide—is formed, along with an unexpected allyl hydroxylation product—N-[2-(6-hydroxycyclohex-1-en-1-yl)-6-methylphenyl]-4-methylbenzenesulfonamide.

全文:

受限制的访问

作者简介

Rail Safargalin

Ufa Institute of Chemistry of the Ufa Federal Research Center of the RAS

编辑信件的主要联系方式.
Email: gataullin@anrb.ru
ORCID iD: 0009-0007-9462-9027
俄罗斯联邦, 71, Oktyabr Ave., Ufa, 450054

Rail Gataullin

Ufa Institute of Chemistry of the Ufa Federal Research Center of the RAS

Email: gataullin@anrb.ru
ORCID iD: 0000-0003-3269-2729
俄罗斯联邦, 71, Oktyabr Ave., Ufa, 450054

参考

  1. Wray B.C., Stambuli J.P. Org. Lett. 2010, 12, 4576–4579. doi: 10.1021/ol101899q
  2. Counceller C.M., Eichman C.C., Wray B.C., Stambuli J.P. Org. Lett. 2008, 10, 1021–1023. doi: 10.1021/ol800053f
  3. Galimova Z., Smirnova I., Lobov A., Polovyanenko D., Rybalova T., Kazakova O. Int. J. Mol. Sci. 2024, 25, 8356. doi: 10.3390/ijms25158356
  4. Мясоедова Ю.В., Назаров И.С., Ишмуратов Г.Ю. ЖОрХ. 2019, 55, 67–99. [Myasoedova Y.V., Nazarov I.S., Ishmuratov G.Y. Russ. J. Org. Chem. 2019, 55, 47–73.] doi: 10.1134/S107042801901007X
  5. Мясоедова Ю.В., Нуриева Э.Р., Гарифуллина Л.Р., Ишмуратова Н.М., Ишмуратов Г.Ю. ЖОрХ, 2021, 57, 109–114. [Myasoedova Yu.V., Nurieva E.R., Garifullina L.R., Ishmuratova N.M., Ishmuratov G.Yu. Russ. J. Org. Chem. 2021, 57, 113–116.] doi: 10.1134/S1070428021010164
  6. Paioti P.H.S., Rezende P., Coelho F. J. Braz. Chem. Soc. 2012, 23, 285–293. doi: 10.1590/S0103-50532012000200014
  7. Hilt G., Arndt M., Weske D.F. Synthesis. 2010, 1321-1324. doi: 10.1055/s-0029-1219278
  8. Hilt G. Synlett. 2011, 1654–1659. doi: 10.1055/s-0030-1260800
  9. Ишмуратов Г.Ю., Харисов Р.Я., Яковлева М.П., Боцман О.В., Муслухов Р.Р., Толстиков Г.А. Извес-тия АН. Сер. хим. 1999, 198–199. [Ishmuratov G.Yu., Kharisov R.Ya., Yakovleva M.P., Botsman O.V., Muslukhov R.R., Tolstikov G.A. Russ. Chem. Bull. 1999, 48, 197–198.] doi: 10.1007/BF02494428
  10. Ишмуратов Г.Ю., Харисов Р.Я., Яковлева М.П., Боцман О.В., Муслухов Р.Р., Толстиков Г.А. ЖОрХ. 2001, 37, 49–50. [Ishmuratov G.Yu., Kharisov R.Ya., Yakovleva M.P., Botsman O.V., Muslukhov R.R., Tolstikov G.A., Russ. J. Org. Chem. 2001, 37, 37–39.] doi: 10.1023/A:1012313114674
  11. Хуснитдинов Р.Н., Султанов Р.М., Гатауллин Р.Р. ЖОХ. 2021, 89, 511–521. [Khusnitdinov R.N., Sultanov R.M., Gataullin R.R. Russ. J. Gen. Chem. 2019, 89, 653–662.] doi: 10.1134/S1070363219040030
  12. Gataullin R.R. Tetrahedron. 2021, 96, 132388. doi: 10.1016/j.tet.2021.132388
  13. Eržen E., Cerkovnik J., Plesničar B. J. Org. Chem. 2003, 68, 9129–9131. doi: 10.1021/jo035154m
  14. Avzyanova E.V., Timerghazin Q.K., Khalizov A.F., Khursan S.L., Spirikhin L.V., Shereshovets V.V. J. Phys. Org. Chem. 2000, 13, 87–96. doi: 10.1002/(SICI)1099-1395(200002)13:2<87::AID-POC210>3.0.CO;2-D
  15. Khursan S.L. PATAI’S Chem. Functional Groups. doi: 10.1002/9780470682531.pat0874
  16. Gataullin R.R. Russ. J. Org. Chem. 2023, 59. 2157–2166. doi: 10.1134/S1070428023120138

补充文件

附件文件
动作
1. JATS XML
2. Scheme 1

下载 (222KB)
3. Scheme 2

下载 (182KB)
4. Figure. Inferred decay fragment structures of protonated and deprotonated alcohol molecular ion 5 under mass spectrometry conditions.

下载 (386KB)

版权所有 © Russian Academy of Sciences, 2025