{(E)‐ and {(Z)‐2‐[α,β‐bis(methoxycarbonyl)vinyl]cyclopentadien‐1‐ylidene}triphenylphosphorane |
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Authors: | Lee J Higham P Gabriel Kelly Helge Müller‐Bunz Declan G Gilheany |
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Abstract: | The Ramirez ylide undergoes electrophilic substitution with dialkyl acetylenedicarboxylates, yielding a mixture of the Z and E adducts. The crystal structure analyses of the two adducts formed using dimethylacetylene, viz. dimethyl (E)‐ and (Z)‐1‐2‐(triphenylphosphoranylidene)cyclopentadien‐1‐yl]ethylenedicarboxylate, both C29H25O4P, explain an unusual chemical shift observed for the vinyl H atom of the Z adduct, which had previously precluded a definitive assignment of the isomers. In addition, the structures explain why only one of the isomers reacts further with acetylene esters to produce azulenes with a rare substitution pattern. |
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