Metathesis and metallotropy: a versatile combination for the synthesis of oligoenynes.
We have demonstrated that the combined use of enyne metathesis and metallotropic [1,3]-shift of the corresponding alkynyl ruthenium carbenes is a powerful synthetic tool to construct oligoenynes. In this reaction, alkynyl carbene intermediates formed from an initial ring-closing metathesis reaction (RCM) undergo repetitive [1,3]-shifts and RCMs to give the final products. Linear poly-1,3-diynes containing repeating functionality of the type -[XCH2CCCCCH2]n- generated long-chain conjugated oligoenynes up to n = 5.
Kim
Mansuk
M
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
Lee
Daesung
D
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry
D000475:Alkenes; D000480:Alkynes; D012428:Ruthenium