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

被引：4

作者：

Morgans, Garreth L. ^{[1
]}

Yadav, Dharmendra B. ^{[1
]}

Fernandes, Manuel A. ^{[1
]}

de Koning, Charles B. ^{[1
]}

Michael, Joseph P. ^{[1
]}

van Otterlo, Willem A. L. ^{[1
]}

机构：

[1] Univ Witwatersrand, Sch Chem, Inst Mol Sci, ZA-2050 Po Wits, Johannesburg, South Africa

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 19期

基金：

新加坡国家研究基金会;

关键词：

Ring-closing metathesis; Benzothiazocine; Benzothiazine; Ruthenium carbene; Rearrangements; RING-CLOSING METATHESIS; ISOMERIZATION; DERIVATIVES; CARBENE;

D O I：

10.1016/j.tetlet.2012.02.109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 expected product, 6-1(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)-benzene-sulfonamide in the same reaction gave 2-(2-methyl-2-propenyl)-3,4-dihydro-2H-1,4-benzothiazine. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2384 / 2387

页数：4