Unsaturated gamma-Thiolactones. V. On the Rearrangement of Some 5-Alkyl-substituted Thiolene-2-ones.

Hörnfeldt, Anna‐Britta; Wanger, Marianne; Carter, Robert E.; Corrodi, H.; Eriksson, G.; Blinc, R.; Paušak, S.; Ehrenberg, L.; Dumanović, J.

doi:10.3891/acta.chem.scand.21-0673

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“…It might at first appear that the synthesis of suitable subunits used in the construction of compounds A can be accomplished using a Williamson's ether synthesis. However, the well-known Williamson's ether synthesis of alkoxyphenyl systems has little counterpart when compared with 2-thienyl systems such as 2-hydroxythiophene. − …”

Section: Introductionmentioning

confidence: 99%

Troublesome Alkoxythiophenes. A Highly Efficient Synthesis via Cyclization of γ-Keto Esters

et al. 2001

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A variety of alkoxythiophenes have been synthesized that represent ideal subunits for the synthesis of a new class of thermotropic liquid crystals via palladium-catalyzed cross-coupling reactions and organometallic derivatization. The methodology used represents the first highly efficient synthesis of alkoxythiophenes unlike previous pathways that have presented serious synthetic difficulties when the alkoxy chain consisted of more than four carbon atoms. The scope of the new procedure (relative to liquid crystalline intermediates) is presented and is compared and contrasted with the current literature.

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