The cycloadditions of nitrosoketene with formaldehyde, acetone and 2-propenal were calculated using ab initio molecular orbital theory (MP2/6-31G*). The reactions proceed by the [3+2] pathway via a concerted, planar and pseudopericyclic transition state with a significantly lower barrier rather than by the alternative [4+2]. The transition state asynchronicity can be used to explain the substituent effects on the cycloaddition of ketones with nitrosoketene.
|Number of pages||4|
|State||Published - Aug 1997|