Add time:08/19/2019         Source:sciencedirect.com

The reductive trimethylsilylation of 1,4-bis(trimethylsilyl)benzene to 1,3,4,6-tetrakis(trimethylsilyl)-1,4-cyclohexadiene(III) and of p-dibromo- and p-dichlorobenzenes to (III) and in addition to 1,4,5,6-tetrakis(trimethylsilyl)-1,3-cyclohexadiene(IV) and 3,3,6,6-tetrakis(trimethylsilyl)-1,4-cyclohexadiene(VI) is described. The proposed mechanism involves anion radical intermediates. An attempted preparation of (VI) by metalation of the methine hydrogens of 3,6-bis(trimethylsilyl)-1,4-cyclohexadiene(I) and derivatization with chlorotrimethylsilane was unsuccessful; only partial dehydrogenation of (I) to 1,4-bis(trimethylsilyl)benzene occurred.

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