Generation of medium-ring cycloalkynes by ring expansion of vinylogous acyl triflates

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1572-1575

  Tummatorn, Jumreang ^a   Dudley, Gregory B ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952601041     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2003308     Document Type: Article

References (58)

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41. 1H NMR spectrum of 2 displays unusually broad resonance signals suggestive of a complex mixture of conformational isomers (see p S27 of the Supporting Information for a copy of the spectrum).
42. This concentration corresponds to slightly more than 2 mg of substrate per mL of solvent. In our hands, the reaction becomes impractical below this concentration.
43. We speculate that these cyclization pathways are compromised by angle strain and transannular interactions, respectively, and that decomposition through competing pathways involving the vinyl triflate may be occurring. Our initial attempts to generate cyclooctynes by this method were unsuccessful, and further efforts are in progress.
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