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The silenes A and B are formed by reacting 1,3-di t butyl-2,4-dichloro-2,4-divinyl-1,3-diaza- 2.4-disilacyclobutane (2) and 1,3-dichloro-2,4-dineopentyl-1,3-divinyl-1,3-disilacyclobutane (15) with LiBu t  in n-pentane in the temperature range from −10 to 0 °C. The reaction primarily leads to the corresponding α-lithioadducts (addition of LiBu t  to the vinyl group of 2 and 15), and with subsequent 1,2-LiCl elimination yields A and B as intermediates. A can be trapped by polar reagents Me 3 SiX (X = OMe, OSO 2 CF 3 ) as well as by organic dienes which add across the Si = C bond; in the absence of a trapping agent the spiro compound 6 is isolated. The silenes A and B differ in their cycloaddition behaviour to butadienes, norbornadiene and cyclohexa-1,3-diene: Whereas for A the regioselective [2 + 2]-cycloaddition to yield monosilacyclobutane derivatives is preferred due to electronic reasons, the reaction of B leads mainly to Diels-Alder products. Thus, A is quite comparable in its reactivity to dichloroneopentylsilene, while B reacts like its diorgano substituted analogues R 2 Si = CHCH 2 Bu t  (R = Me, Bu t  or Ph).

zeitschrift für naturforschung b

Silaheterocyclen, XIII Erzeugung und Cycloadditionsverhalten von 1,3-Diaza-2,4-disila-und 1.3-Disilacyclobutanen mit exocyclischer SiC-Doppelbindung Silaheterocycles, XIII / Formation and Cycloaddition Reactions of 1,3-Diaza-2,4-disila-and 1.3-Disilacyclobutanes Containing an Exocyclic SiC Double Bond