Allylic amination of alkenes by tosyliminoiodobenzene: manganese porphyrins as suitable catalysts

✍ Scribed by J.P. Mahy; G. Bedi; P. Battioni; D. Mansuy

• Book ID: 104217524
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 275 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82081-x

✦ Synopsis

Manganese-porphyrins and particularly Mn(TPP)(C104) were found to be much better catalysts than iron-porphyrins for allylic N-tosylamination of alkenes by tosyliminoiodobenzene. With the former catalysts, cyclohexene was selectively transformed into 3-tosylaminocyclohexene with yields up to 70% and cis-and trans-hex-2-ene into allylic N-tosylamines with yields around 40X, whereas cyclooctene led to the corresponding allylic and homoallylic N-tosylamines. 2!40(dt,2H) ; 2.42(s,3H) ; 4.18(m,lH) ; 4.34(d,lH,J*9.6Hs) ; 5.l(m,lH) ; 5.58(m,lH) ; 7.26(d,2H,J=7.5Hz) ; 7.74(d,2H,J=7.5Hs). : m/z~91(100%1 ; 124(35X) ; 155(23X) ; 184(25X) ; 210(15%) ; 236(21%) .; 279(25X) ; &;";$H ; 2.08(dd,2H) ; 2.4l(s,3H) ; 3.44(m,lH) ; 4.35(d,lH,J=lOHs) ; 5.48(m,lH) ; -m, ; 7.29(d,2H,J=7.5Hz) ; 7.75(d,2H,J=7.5Hs). a) Groves, J.T.