Journal
ORGANIC LETTERS
Volume 11, Issue 14, Pages 3076-3079Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol901148p
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [19675001, 17069011]
- Grants-in-Aid for Scientific Research [17069011] Funding Source: KAKEN
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Upon the treatment of bis(arylcarbonyl)diphenylacetylenes with lithium naphthalenide, the carbonyl reduction dominantly occurs over the acetylene reduction. The produced bis(radical anion) intermediate undergoes a synchronous double-radical 5-endo-dig cyclization. This simple reduction procedure produces two intriguing classes of ladder pi-conjugated skeletons, i.e., emissive methylene-bridged stilbenes and dibenzo[a,e]pentalenes regarded as a cyclic 1,4-diphenylbutadiene.
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