61985-88-4Relevant articles and documents
Cycloaddition Reactions of Heterocumulenes, XXVIII. - A 1,6-Dipole Stabilized by No-Bond Resonance. - Molecular Structure and Reactivity
Schaumann, Ernst,Kausch, Erwin,Klaska, Karl-Heinz,Klaska, Rolf,Eck, Joachim
, p. 405 - 410 (2007/10/02)
The X-ray structural investigation of the 1,6-dipole 1 reveals an intramolecular S-N contact of 236 pm, which indicates stabilization by no-bond resonance.In reactions with the heterocumulenes 2-5, the thiazoline ring of 1 is opened to give the heterocycles 7a-f, 8e.The reaction of bis(trimethylsilyl)thioketene (6) takes a deviating pathway: the primary adduct 15 gives a sigmatropic 1,3 shift of the dimethylamino group to yield product 16b.This constitution is derived from an X-ray structural study of the degradation product 17.