Abstract
Simple β-hydroxy-γ-phenylsulfanyl nitriles
undergo a selective Ritter reaction, onto a thiiranium (episulfonium)
ion, to yield 15-membered triamides. This selective trimerisation
allows the rapid synthesis of these macrocylic triamides.
Keywords
amides - sulfur - Ritter reaction - macrocycles - ring closure - thiiranium Ions
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Crystallographic
data for the syn-amide
24 : C12 H17 NOS, Monoclinic,
space group P2(1)/c. a = 15.6767(9) Å, b = 8.9827(6) Å,
c = 18.7004(11) Å, β = 107.086(4)°, V = 2517.1(3) Å3 ,
Z = 8, Dc = 1.179
Mg/m3 , µ = 0.233mm-1 ,
F(000) = 960, Data (12949 reflections collected,
3269 independent reflections Rint = 0.0793)
were measured on a Nonius Kappa CCD diffractometer at 180(2) K.
Refinement Method Full-matrix least-squares on F2 , [R1 = 0.1021
(I >2σI), ωR2 = 0.2183],
Goodness-of-fit on F2 1.038. The crystals were
small and of poor quality, hence the relatively high R-factors.
