%0 Generic
%A Czekelius, Constantin
%A Hafer, Jillian
%A Tonzetich, Zachary J.
%A Schrock, Richard R.
%A Christensen, Ronald L.
%A Müller, Peter
%D 2006
%T Synthesis of Oligoenes that Contain up to 15 Double Bonds
from 1,6-Heptadiynes
%U https://acs.figshare.com/articles/dataset/Synthesis_of_Oligoenes_that_Contain_up_to_15_Double_Bonds_from_1_6_Heptadiynes/3038122
%R 10.1021/ja0656705.s001
%2 https://ndownloader.figshare.com/files/4741531
%K 15 Double Bonds
%K Oligoene
%K bimetallic Mo bisalkylidene species
%K isopropylidene unit
%K bimetallic species
%K synthesis
%K yields 3 b 2.
%K 3 b 6
%K monometallic Mo alkylidene
%K McMurry
%K 3 b 7
%K oligoenes range
%K monomeric
%K bimetallic Mo alkylidene
%K representative aldehyde
%X This paper reports the synthesis of polyene oligomers (“oligoenes”) that contain up to 15 double
bonds that are identical to the “all five-membered ring” species formed through cyclopolymerization of
diisopropyldipropargylmalonate. The oligoenes contain an isopropylidene unit at each end. The isolated
oligoenes range from the “dimer” (a pentaene, (E)-di-1,2-[1-(2-methyl-propenyl)-4,4-di-iso-propyl-carboxy-cyclopent-1-enyl]-ethene (3b2)) to the “heptamer” (3b7, a pentadecaene). Oligoenes 3b2, 3b3, 3b4, 3b5,
and 3b7 were prepared through Wittig-like reactions between aldehydes and the appropriate monometallic
Mo alkylidene or bimetallic Mo bisalkylidene species whose alkylidene is derived from an identical five-membered ring monomeric unit. Compounds 3b2, 3b4, and 3b6 were prepared through McMurry coupling
reactions of aldehydes. A representative aldehyde (the “monomeric” aldehyde) is diisopropyl-3-formyl-4-(2-methylprop-1-enyl)cyclopent-3-ene-1,1-dicarboxylate (2b), McMurry coupling of which yields 3b2. A
heptaene that contains a six-membered ring in the central unit also was prepared in a Wittig-like reaction
involving a bimetallic Mo alkylidene; this species is a model for oligoenes that contain both six-membered
and five-membered rings. X-ray structures of two bimetallic species that are employed in the synthesis of
the oligoenes are reported.
%I ACS Publications