Owen Summerscales - C-H Activation of Cycloalkenes by Dimetallynes (M = Ge, Sn) under Ambient Conditions

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      Publication Details (including relevant citation   information):

      J. Am. Chem. Soc. 2011, 133,   11960-11963

      Abstract:

        Treatment of the dimetallynes   Ar′EEAr′ [E = Ge, Sn; Ar′ = C6H3-2,6-(C6H3-2,6-iPr2)2] with a   cyclic olefin—cyclopentadiene (CpH), cyclopentene,   1,4-cyclohexadiene (CHD), or cyclohexene—showed that, with the   exception of cyclohexene, they react readily, affording C–H   activation at room temperature. Reaction of the digermyne and   distannyne with CpH gave the cyclopentadienyl anion, which is   bound in a π-fashion to a mononuclear group 14 element center,   along with evolution of hydrogen gas. Unusually, the digermyne   also reacted with cyclopentene to give the same   dehydroaromatization product, formed from triple C–H   activation/dehydrogenation. It also was found to react with CHD   to give a mixture of (Ar′GeH)2, benzene, and a new   7-germanorbornadiene species bound to a cyclohex-2-enyl   fragment.

      Address (URL): http://pubs.acs.org/doi/abs/10.1021/ja205816d