The preparation of a diverse array of enantiomerically
pure 1- and 2-sulfinyl dienes has been
achieved via Stille coupling of halovinyl sulfoxides and vinyl
stannanes, hydrogenation of 1-sulfinyl-1-en-3-ynes, or vinylcupration of 1-sulfinyl alkynes. Formation of
the corresponding sulfinyl diene
iron(0) tricarbonyl complexes was accomplished by utilizing
Fe(CO)5/NMO or (bda)Fe(CO)3 as
iron(0)
tricarbonyl transfer reagents. Installation of the iron(0)
tricarbonyl fragment was shown to be
highly diastereoselective (10−16:1) for
(R)-(1Z)-1-sulfinyl dienes, most likely as a
result of allylic
1,3-strain. The synthesis of a 1-sulfinyl-1,3,8,10-tetraene is
also described.
Polarized optical microscopy image of a fingerprint texture for a lyotropic chromonic liquid crystal entering the chiral nematic–isotropic coexistence region. The helical axis is in the plane of the image and the perpendicular distance between the stripes is around 50 μm, half the chiral nematic pitch.
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