Nitrosoolefins are unstable intermediates in nucleoplilic substitutions at bischloronitroso compounds and a-chlorooximes [ l -31. They react rapidly with nucleophilic agents; in the absence of such agents they rearrange by a proton shift to oximes of &$-unsaturated carbonyl compounds. A further possible reaction of monomeric nitrosolefins is the polymerisation to tarry compounds. Monomeric nitrosoolefins can be isolated only in the absence of strong nucleophiles and if their structure makes both a rearrangement and a polymerisation impossible. So we succeeded in the preparation of three 2,6disubstituted 1-phenyl-2-nitroso prop 1-enes [4], and later the isolations of 1-nitroso 2,2-di-tert-butyl ethylene [5] and 1,ldichloro-2-nitroso prop-1-ene [6] were also accomplished.In our earlier work [4] we did not succeed in determining the configuration of the 1-aryl-2-nitroso prop-1-enes prepared, and it remained uncertain whether a stabilization of the compounds by mesomerism of the nitroso olefin group with the aromatic nucleus takes place. The position and the extinction coefficient of the n-r* band in the region of about 700 nm seemed to be arguments for a stabilization of these nitrosoolefins by mesomerism with the aromatic nucleus. On the other hand the substituents in 2-and 6-position of the phenyl group make a coplanar arrangement of the aromatic ring and the nitrosolefin system very improbable.We have once again prepared the nitrosoolefins lbd described in [4] and moreover 1-(2,6-dimethylphenyI)-2nitroso prop-1-ene l a in order to elucidate their structure by X-ray analysis. Only in the case of 1-(2-methoxy-4,6-1 Formula Scheme 1 Structure of 1-(2-methoxy-4,6-dimethylphenyl)-2-nitroso prop-1-ene Id. The plane of the nitrosoolefin side chain is twisted out of the plane of the aromatic nucleus with an angle of (49.3 i 0.2)". Table 1 13C-and 'H-nmr signals of the nitrosoolefins la-d Ar\ /CH3 1 b Ar : 2,4,64rirnethylphenyI
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