σ-Bonded silyl-, germyl-, stannyl derivatives
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Symmetrically 4,16-disubstituted (3a-c) and bridged (6a, b) organometallic paracyclophane derivatives have been synthesized for use as monomeric precursors of organometallic poly-p-xylylenes. Both types of compounds were obtained by lithiation of the appropriately substituted paracyclophane bromides (1 or 4) and subsequent quenching of the resulting lithioparacyclophane derivatives with organometallic electrophiles. For the synthesis of 4,16-bis(trimethylsilyl)[2.2]paracyclophane (3a) we also examined the Grignard reaction, and as a result the first successful use of a 4,16-bis Grignard reagent is described. According to the spectral data, the bridged compounds 6a, c are formed as diastereomeric mixtures of a meso- and a d,l form. The diastereomers were separated by fractional recrystallization and characterized.
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