Formation of an unexpected rearrangement product using Grubbs鈥?second generation catalyst: 2-allyl-3,4-dihydro-2H-1,4-benzothiazines from diene precursors

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• 作者：Garreth L. Morgans^a ; Dharmendra B. Yadav^a ; Manuel A. Fernandes^a ; Charles B. de Koning^a ; Joseph P. Michael^a ; Willem A.L. van Otterlo^a ; ^b ; ^{wvo@sun.ac.za} ; ^{Willem.vanOtterlo@wits.ac.za}
• 关键词：Ring-closing metathesis ; Benzothiazocine ; Benzothiazine ; Ruthenium carbene ; Rearrangements
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：9 May, 2012
• 卷：53
• 期：19
• 页码：2384-2387
• 文件大小：737 K

摘要

Application of sub-stoichiometric amounts of Grubbs鈥?second generation catalyst to the substrate N-allyl-N-[2-(allylsulfanyl)phenyl]-4-methylbenzenesulfonamide afforded the ring-closed compound 6-[(4-methylphenyl)sulfonyl]-5,6-dihydro-2H-1,6-benzothiazocine, as well as the unexpected 2-allyl-4-[(4-methylphenyl)sulfonyl]-3,4-dihydro-2H-1,4-benzothiazine. Use of similar conditions on an analogous sulfoxide resulted in the expected product, 6-[(4-methylphenyl)sulfonyl]-5,6-dihydro-2H-1,6-benzothiazocine 1-oxide, indicating that the sulfide was playing a key role in this novel transformation. Furthermore, the use of N-allyl-4-methyl-N-{2-[(2-methyl-2-propenyl)sulfanyl]phenyl}-benzenesulfonamide in the same reaction gave 2-(2-methyl-2-propenyl)-3,4-dihydro-2H-1,4-benzothiazine.