1993
DOI: 10.1021/ja00057a020
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Cyclopentenone formation via hydrogen activation in the reactions of chromium carbene complexes with alkynes

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Cited by 51 publications
(12 citation statements)
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“…An unusual double bond carbon signal observed in the downfield region at δ C 174.0 (C-9) of the 13 C NMR spectrum, together with signals at δ C 207.0 (C-12), 139.2 (C-13), 78.0 (C-10), and 40.5 (C-11), suggested the presence of a conjugated cyclopentenone structure, which was supported by comparison with reported NMR data of a similar ring system (Challener, 1993). The carbonyl carbon signal at δ C 174.1 (C-1) and seven methylene signals at δ C 34.0 (C-2), 29.7 (C-6), 29.0 (C-4 and 5), 28.1 (C-7), 27.4 (C-8), and 24.9 (C-3), were assignable to a fatty acid chain moiety.…”
Section: Resultssupporting
confidence: 80%
“…An unusual double bond carbon signal observed in the downfield region at δ C 174.0 (C-9) of the 13 C NMR spectrum, together with signals at δ C 207.0 (C-12), 139.2 (C-13), 78.0 (C-10), and 40.5 (C-11), suggested the presence of a conjugated cyclopentenone structure, which was supported by comparison with reported NMR data of a similar ring system (Challener, 1993). The carbonyl carbon signal at δ C 174.1 (C-1) and seven methylene signals at δ C 34.0 (C-2), 29.7 (C-6), 29.0 (C-4 and 5), 28.1 (C-7), 27.4 (C-8), and 24.9 (C-3), were assignable to a fatty acid chain moiety.…”
Section: Resultssupporting
confidence: 80%
“…The only enyne−carbonyl compound that failed to produce a furan derivative was the enyne ester (Table , entry D). Neither starting material was recovered from this reaction; no identifiable compounds could be isolated from this complex reaction mixture . This failure is presumably due to the lower nucleophilicity of the carbonyl oxygen; thus, the crucial cyclization to the carbonyl ylide intermediate does not occur.…”
mentioning
confidence: 98%
“…tion of a chromium alkenyl carbene complex can be also achieved if a silicon group is present in the b-position[26].…”
mentioning
confidence: 99%