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Mechanistyczne aspekty nieuzgodnionych (4+2)[pi]-elektronowych cykloaddycji

Jasiński R., Kwiatkowska M., Barański A.

Wiadomości Chemiczne

2007

[Z] 61, 7-8

485-514

In this work the reported in literature (4+2)[pi]-electron cycloadditions, where a two-step mechanism was postulated and more or less thoroughly documented, has been subjected to a critical analysis. The research has been focused on [2+3] and [2+4] cycloadditions. To-date not many detailed studies, which would lead to unambiguous conclusions have been performed in this area. The two-step reaction mechanism of thiocarbonylylides with 1,2-dicyanoethene derivatives, [pi]-deficient cyclic ylides with 1-(dimethylamino)-propyne and 1,1-dimethoxy-1,3-butadiene with [pi]-deficient ethene derivatives can be considered as the most documented ones. On the other hand, the reports where a non-concerted mechanism of [2+3] cycloaddition of nitrile oxides with dideuteroethenes and [2+4] cycloaddition of 2-methylfurane with 1,2-dicarboxyethene was postulated are less reliable.