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

Selective derivatization and characterization of bifunctional “Janus-Type” cyclotetrasiloxanes
Selective derivatization and characterization of bifunctional “Janus-Type” cyclotetrasiloxanes
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)-OSiMe(2)Vin](4)) and for the coupling product 21 ([biphenyl-CC-C6H4-Si(O)-OSiMe(2)Vin](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.
0276-7333
1732-1742
Panisch, Robin
006fcba0-e699-4b5a-9564-b6fcf7815850
Bassindale, Alan R.
285ee4e0-58d0-4178-a0d9-d7e0d1efbebd
Korlyukov, Alexander A.
2456dc2b-9244-4a01-9e40-acb838822e93
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Taylor, Peter G.
e59508fd-4cfb-422c-bbb0-b70cfb6aa195
Panisch, Robin
006fcba0-e699-4b5a-9564-b6fcf7815850
Bassindale, Alan R.
285ee4e0-58d0-4178-a0d9-d7e0d1efbebd
Korlyukov, Alexander A.
2456dc2b-9244-4a01-9e40-acb838822e93
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Taylor, Peter G.
e59508fd-4cfb-422c-bbb0-b70cfb6aa195

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), 1732-1742. (doi:10.1021/om301158w).

Record type: Article

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)-OSiMe(2)Vin](4)) and for the coupling product 21 ([biphenyl-CC-C6H4-Si(O)-OSiMe(2)Vin](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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More information

Published date: 25 March 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 362493
URI: http://eprints.soton.ac.uk/id/eprint/362493
ISSN: 0276-7333
PURE UUID: 15744cfa-8480-42a3-914f-6d6102595595
ORCID for Mateusz B. Pitak: ORCID iD orcid.org/0000-0002-3680-7100
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 25 Feb 2014 14:26
Last modified: 18 Feb 2021 16:53

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Contributors

Author: Robin Panisch
Author: Alan R. Bassindale
Author: Alexander A. Korlyukov
Author: Mateusz B. Pitak ORCID iD
Author: Simon J. Coles ORCID iD
Author: Peter G. Taylor

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