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

…, MA Fernandes, CB de Koning, JP Michael…

Index: Morgans, Garreth L.; Yadav, Dharmendra B.; Fernandes, Manuel A.; De Koning, Charles B.; Michael, Joseph P.; Van Otterlo, Willem A.L. Tetrahedron Letters, 2012 , vol. 53, # 19 p. 2384 - 2387

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Citation Number: 5

Abstract

Application of sub-stoichiometric amounts of Grubbs' 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 ...