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Volumn 49, Issue 31, 2008, Pages 4596-4600

β-Halovinylsilanes in oligoyne synthesis: a fluoride-catalysed unmasking of alkynes from β-fluorovinylsilanes

Author keywords

Elimination; Oligoynes; Polyynes; Tin halogen exchange; Vinylsilanes

Indexed keywords

ALKYNE; BETA FLUOROVINYLSILANE; BETA HALOVINYLSILANE; FLUORIDE; OLIGOYNE; REAGENT; SILANE DERIVATIVE;

EID: 45049087475     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.081     Document Type: Article
Times cited : (10)

References (82)
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    • We have recently used this reagent in a completely stereoselective synthesis (retention of configuration) of a (Z)-β-bromovinylsilane:. Williams I., Kariuki B.M., Reeves K., and Cox L.R. Org. Lett. 8 (2006) 4389-4392
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    • note
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    • For some recent examples of NBS-mediated bromodestannylation reactions proceeding with retention of configuration:. Gracia J., and Thomas E.J. J. Chem. Soc., Perkin Trans. 1 (1998) 2865-2871
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    • 2, which proceed with retention of configuration:
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    • note
    • Crystallographic data (excluding structure factors) for 10 have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publications No. CCDC 686832. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0)1223-336033 or email: deposit@ccdc.cam.ac.uk).
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    • note
    • Unmasking was only performed on phenyl end-capped masked hexayne 22 and not on TMS end-capped analogue 21. Under the conditions used to effect defluorosilylation, removal of the TMS end-caps in 21 would also occur to provide an extremely unstable free hexayne. Since the TMS protecting groups can be removed without inducing dehalosilylation, 21 represents a convenient monomer precursor for oligomerisation studies.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.