Construction of eight-membered carbocycles by palladium-catalyzed [4 + 4] cycloaddition of vinylallenes

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 951-953

  Murakami, Masahiro ^a   Itami, Kenichiro ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Carbocycles; Eight membered ring; Palladium; Vinylallenes; 4 + 4 cycloaddition

Indexed keywords

ALLENE DERIVATIVE; PALLADIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CONJUGATION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032978785     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3087     Document Type: Article

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47. 2 carbon atoms significantly reduced the repulsive interactions between the two neighboring exocyclic isopropylidene groups.
48. 2-Phenyl-1,3,4-hexatriene, vinylallene having only one methyl group at the allene terminus, also underwent palladium-catalyzed cycloaddition facilely to afford a [4 + 4] cycloadduct (a mixture of stereoisomers with respect to the orientation of the methyl groups of the exocyclic double bonds) together with a small amount of a [4 + 2] cycloadduct. Unfortunately, these products could not be separated by Chromatographie techniques including HPLC.
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