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The silene Cl 2 Si=C(Ph)CH 2 Bu t  (2) is formed by the reaction of 1,1,1-trichloro-2-phenyll- silaprop-2-ene (1) with LiBu t  in n-pentane in the temperature range from -15 to 0 °C. The reaction initially leads to the corresponding α-lithio adduct A (addition of LiBu t  to the vinyl group of 1); subsequent LiCl elimination yields 2 as an intermediate. 2 can be trapped by Me 3 SiOMe (3) and dienes which add across the Si=C bond. In the absence of trapping agents but in the presence of the Lewis base NEt 3  the mixture 1/LiBu t  reacts to give the disilacyclobutane 4. Due to its electronic and steric properties, Cl 2 Si=C(Ph)CH 2 Bu t  (2) and butadienes yield mainly the Diels-Alder adducts (5, 7, 9) while with styrene and 1,3-cyclohexadiene the [2+2] and [4+2] products are formed in competition. With 2-norbornene, 2,5-norbornadiene and quadricyclan the [2+2] and [2+2+2] products are formed selectively but only in low yields. In all reactions except with quadricyclan an ene-reaction competes with the cycloaddition leading to ene-compounds as by-products

zeitschrift für naturforschung b

Silaheterocyclen, XXVII. Substituenteneffekte zur Steuerung des Cycloadditionsverhaltens von Silaethenen [1] / Silaheterocycles, XXVII. Controlling the Cycloaddition Behavior of Silenes by Substituent Effects [1]