Intramolecular Reductive Double Cyclization of o,o′-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons

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 pro...

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Published inOrganic letters Vol. 11; no. 14; pp. 3076 - 3079
Main Authors Zhang, Hongyu, Karasawa, Takashi, Yamada, Hiroshi, Wakamiya, Atsushi, Yamaguchi, Shigehiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.07.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HETEROCYCLES
SILICON
CONSTRUCTION
CARBOALKOXYLATION
STILBENES
ALKYNES
DERIVATIVES
5-ENDO-DIG CYCLIZATION
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Summary: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 π-conjugated skeletons, i.e., emissive methylene-bridged stilbenes and dibenzo[a,e]pentalenes regarded as a cyclic 1,4-diphenylbutadiene.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol901148p