Selective derivatization and characterization of bifunctional “Janus-type”cyclotetrasiloxanes

Panisch, Robin; Bassindale, Alan R.; Korlyukov, Alexander A.; Pitak, Mateusz B.; Coles, Simon J. and Taylor, Peter G. (2013). Selective derivatization and characterization of bifunctional “Janus-type”cyclotetrasiloxanes. Organometallics, 32(6) pp. 1732–1742.

DOI: https://doi.org/10.1021/om301158w

Abstract

Stereoregular all-cis cyclotetrasiloxanes [R-Si(O)-R']₄ with different functional groups attached to the opposite faces of the ring skeleton were derivatized without stereoisomerization or cleavage of the (SiO)]₄ ring and with high selectivity using standard synthetic methods. The solid-state structures obtained for the iodophenylsubstituted starting material 16 ([p-I-C₆H₄-Si(O) OSiMe₂Vin]₄) and for the coupling product 21 ([biphenyl-CC-C₆H₄-Si(O) OSiMe₂Vin]₄) show a pronounced differentiation in the steric requirements of the different sides of the ring, resulting in characteristic crystal packing. In combination with the observed high thermal and chemical stability, these data demonstrate the high potential of cyclotetrasiloxanes for a wide range of applications.

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