Synthesis and alkyne coordination chemistry of thiacycloalkynes

Kerton, F.M. and Mohmand, G.F. and Tersteegen, Adrian and Thiel, Markus and Went, Michael J. (1996) Synthesis and alkyne coordination chemistry of thiacycloalkynes. Journal of Organometallic Chemistry, 519 (1-2). pp. 177-184. ISSN 0022-328X. (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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The reactions of 1,4-dichlorobut-2-yne with HS(CH2)(n)SH (n = 2-5) or HS(CH2CH2S)(n)H(n = 2-3) or HSCH2CH(OH)CH2SH under high dilution conditions in industrial methylated spirits using KOH as the deprotonating agent produce thiacycloalkynes in remarkably high yields when the 1 : 1 product is a nine-, ten- or 11-membered ring. 1,5-dithiacyclonon-7-yne, 1,5-dithiacyclonon-7-yne-3-ol, 1,6-dithiacyclodec-8-yne, 1,7-dithiacycloundec-9-yne, 1,4,7-trithiacycloundec-9-yne and 1,7-dithia-4-oxa-cycloundec-9-yne are pre pared in yields of 75%, 81%, 79%, 85%, 100% and 95% respectively. The X-ray crystal structures of 1,4-dithiacyclooct-6-yne and 1,6-dithiacyclodec-8-yne have been determined. Selective coordination of the alkyne functionality is demonstrated by the reaction of 1,4,7,10-tetrathiacyclotetradec-12-yne with [Co-2(CO)(8)] to afford a monoalkyne hexacarbonyldicobalt complex and by the reaction of 1,4,7-trithiacycloundec-9-yne with [Mo(CO)(2)(S(2)CNMe(2))(2)] to afford a bisalkynebis(dithiocarbamate)molybdenum complex. A base-catalysed rearrangement of 1,4,7-trithiacycloundec-9-yne affords 2-enyl-1,4,7-trithiacyclonon-2-ene which is an effective ligand for Ag+.

Item Type: Article
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > School of Biosciences
Depositing User: R.F. Xu
Date Deposited: 22 May 2009 16:39
Last Modified: 18 Jul 2014 10:07
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